all 
 known compounds were characterized by h and c nmr and melting point determination ( for solids ) and compared with 
 literature values .
all new compounds were characterized by h , c , f nmr spectra , high - resolution mass 
 spectrometry ( hrms ) , and melting point determination ( for solids ) .
h , c , and f nmr spectra were recorded 
 at 500.4 , 125.8 , and 470.8 mhz , respectively .
hrms ( ci ) data were 
 obtained in positive mode , using ethane as the ionizing gas .
reactions were 
 performed using sealed biotage microwave vials purged with argon several 
 times before use .
reactions were monitored by thin - layer chromatography 
 carried out on silica plates using uv light for visualization .
chromatography 
 was performed on a combiflash rf 200 using hexanes and ethyl acetate 
 as eluent . to 5-bromothienyl-2-sulfonamide ( 242.1 mg , 1.00 mmol ) was added 
 aryl / heteroaryltrifluoroborate ( 1.1 mmol ) , k3po4 ( 636 mg , 3.0 mmol ) , and pd(pph3)4 ( 58 mg , 
 0.05 mmol ) in a vial , which was sealed and purged with argon three 
 times .
then , 1,4-dioxane ( 5 ml ) was added , followed by the addition 
 of h2o ( 1.25 ml ) .
the solution was stirred at 100 c , 
 and the reaction was monitored by gcms / tlc . after the reaction was 
 complete , it was cooled to rt .
extraction was performed with etoac 
 ( 30 ml  3 ) to obtain the organic layer , which was filtered and 
 dried ( na2so4 ) .
the residue obtained was purified by combiflash 
 column chromatography using etoac and hexanes to obtain the desired 
 product .
mp 200201 
 c ; h nmr ( 500 mhz , acetone - d6 )  7.747.69 ( m , 2h ) , 7.647.53
( m , 1h ) , 
 7.517.38 ( m , 4h ) , 6.94 ( br s , 2h ) ; c nmr ( 125.8 
 mhz , acetone - d6 )  150.7 , 145.9 , 
 134.6 , 133.0 , 131.0 , 130.6 , 127.7 , 127.6 , 124.9 , 124.9 ; hrms ( tof 
 ms es ) m / z calcd . for c10h8no2s2 [ m  h ] , 237.9994 ; found , 237.9996 .
mp 185186 
 c ; h nmr ( 500 mhz , acetone - d6 )  7.58 ( dd , j = 4.0 , 1.0 hz , 1h ) , 
 7.44 ( dd , j = 4.0 , 1.0 hz , 1h ) , 7.40 ( br s , 2h ) , 
 7.20 ( br s , 1h ) , 6.87 ( br s , 2h ) , 3.022.88 ( m , 2h ) , 1.29 ( d , j = 7.0 hz , 12h ) ; c nmr ( 125.8 mhz , acetone - d6 )  150.9 , 150.7 , 144.6 , 133.8 , 132.1 , 
 126.3 , 123.8 , 122.6 , 34.8 , 24.2 ; hrms ( tof ms es+ ) m / z calcd . for c16h22no2s2 [ m + h ] , 324.1092 ; found , 324.1088 . obtained as a yellow solid ( 232 mg , 88% ) .
mp 168170 c ; h nmr ( 500 mhz , dmso - d6 )  
 8.27 ( s , 1h ) , 8.04 ( d , j = 8.0 hz , 1h ) , 7.86 ( d , j = 8.0 hz , 1h ) , 7.82 ( br s , 2h ) , 7.00 ( d , j = 3.5 hz , 1h ) , 7.67 ( t , j = 8.0 hz , 1h ) , 7.59 ( d , 
 j = 4.0 hz , 1h ) ; c nmr ( 125.8 mhz , dmso - d6 )  145.6 , 145.1 , 133.6 , 132.2 , 131.0 , 130.6 , 130.5 , 
 129.2 , 125.4 , 118.3 , 112.5 ; hrms ( tof ms es+ ) m / z calcd . for c11h7n2o2s2
mp 170172 
 c ; h nmr ( 500 mhz , acetone - d6 )  7.647.58 ( m , 2h ) , 7.407.37 ( m , 1h ) , 
 7.26 ( dd , j = 9.0 , 2.0 hz , 1h ) ,
7.006.96 
 ( m , 1h ) , 6.85 ( br s , 2h ) , 3.97 ( s , 3h ) , 3.86 ( s , 3h ) ; c nmr ( 125.8 mhz , acetone - d6 )  
 154.7 , 150.7 , 145.4 , 144.5 , 130.3 , 125.1 , 122.9 , 115.8 , 114.2 , 113.5 , 
 56.5 , 55.9 ; hrms ( tof ms es+ ) m / z calcd . for c12h14no4s2
mp 176178 c ; h nmr ( 500 mhz , acetone - d6 )  
 7.56 ( dd , j = 3.5 , 1.5 hz , 1h ) , 7.38 ( dd , j = 4.0 , 1.5 hz , 1h ) , 7.317.24 ( m , 2h ) , 7.207.14 
 ( m , 3h ) , 6.89 ( d , j = 8.0 hz , 1h ) ; c 
 nmr ( 125.8 mhz , acetone - d6 )  158.6 , 
 149.7 , 144.6 , 134.8 , 132.0 , 131.0 , 123.7 , 118.0 , 116.7 , 113.3 ; hrms 
 ( tof ms es+ ) m / z calcd . for c10h8no3s2 [ m  h ] , 253.9946 ; found , 253.9943 . obtained as a yellow solid ( 248 mg , 92% ) . 

mp 180181 c ; h nmr ( 500 mhz , acetone - d6 )  
 7.857.75 ( m , 1h ) , 7.657.50 ( m , 2h ) , 7.407.30 
 ( m , 1h ) , 7.207.10 ( m , 1h ) , 7.107.00 ( m , 1h ) , 6.85 
 ( br s , 2h ) , 3.98 ( s , 3h ) ; c nmr ( 125.8 mhz , acetone - d6 )  156.0 , 144.8 , 144.5 , 130.4 , 130.1 , 
 128.2 , 124.6 , 121.8 , 121.5 , 112.5 , 55.7 ; hrms ( tof ms es+ ) m / z calcd . for c11h12no3s2 [ m + h ] , 270.0259 ; found , 
 270.0254 . obtained as a yellow solid ( 246 mg , 92% ) .
mp 
 177178 c ; h nmr ( 500 mhz , acetone - d6 )  
 10.18 ( s , 1h ) , 7.99 ( d , j = 7.5 hz , 1h ) , 7.797.74 
 ( m , 1h ) , 7.687.62 ( m , 3h ) , 7.26 ( dd , j = 
 7.8 , 3.8 hz , 1h ) , 7.01 ( br s , 2h ) ; c nmr ( 125.8 mhz , 
 acetone - d6 )  191.3 , 147.7 , 144.5 , 
 136.7 , 135.2 , 134.7 , 132.3 , 131.4 , 130.3 , 130.2 , 128.9 ; hrms ( tof 
 ms es+ ) m / z calcd . for c11h9no3s2na [ m + na ] , 
 289.9922 ; found , 289.9924 . obtained as a yellow solid ( 262 mg , 88% ) . 

mp 192193 
 c ; h nmr ( 500 mhz , acetone - d6 )  10.5010.45 ( m , 1h ) , 8.017.95 ( m , 
 2h ) , 7.607.56 ( m , 1h ) , 7.507.42 ( m , 1h ) , 7.377.30 
 ( m , 1h ) , 6.92 ( br s , 2h ) , 4.104.04 ( m , 3h ) ; c 
 nmr ( 125.8 mhz , acetone - d6 )  189.1 , 
 163.2 , 148.6 , 144.9 , 134.3 , 132.4 , 126.7 , 126.0 , 125.8 , 124.0 , 114.4 , 
 56.8 ; hrms ( tof ms es+ ) m / z calcd . 
 for c12h12no4s2 [ m + h ] , 298.0208 ; found , 298.0213 .
mp 
 210212 c ; h nmr ( 500 mhz , acetone - d6 )  9.94 ( s , 1h ) , 7.63 ( dd , j = 4.0 , 1.5 hz , 1h ) , 7.36 ( s , 1h ) , 7.63 ( dd , j = 
 4.0 , 1.5 hz , 1h ) , 7.07 ( s , 1h ) , 6.99 ( br s , 2h ) , 6.24 ( s , 2h ) ; c nmr ( 125.8 mhz , acetone - d6 ) 
  189.4 , 153.4 , 150.2 , 147.8 , 144.3 , 133.9 , 131.4 , 130.8 , 130.4 , 
 111.6 , 106.9 , 104.1 ; hrms ( tof ms es+ ) m / z calcd . for c12h9no5s2na
mp 180181 
 c ; h nmr ( 500 mhz , acetone - d6 )  7.69 ( s , 1h ) , 7.587.56 ( m , 2h ) , 7.447.37 
 ( m , 3h ) , 6.88 ( br s , 2h ) , 4.69 ( br s , 2h ) ; c nmr ( 125.8 
 mhz , acetone - d6 )  150.2 , 145.1 , 
 144.8 , 133.8 , 132.3 , 130.1 , 128.1 , 125.4 , 125.0 , 124.1 , 64.3 ; hrms 
 ( tof ms es+ ) m / z calcd . for c11h10no3s2 [ m  h ] , 268.0103 ; found , 268.0104 .
mp 170171 c ; h nmr ( 500 mhz , acetone - d6 )  
 7.60 ( dd , j = 8.5 , 4.5 hz , 1h ) , 7.47 ( dd , j = 8.0 , 4.0 hz , 1h ) , 7.427.36 ( m , 1h ) , 7.307.22 
 ( m , 2h ) ,
7.01 ( dd , j = 8.0 , 2.5 hz , 1h ) , 6.92 ( br 
 s , 2h ) , 3.89 ( s , 3h ) ; c nmr ( 125.8 mhz , acetone - d6 )  161.2 , 149.7 , 145.1 , 135.0 , 132.1 , 
 131.2 , 124.2 , 119.2 , 115.4 , 112.2 , 55.7 ; hrms ( tof ms es+ ) m / z calcd . for c11h12no3s2 [ m + h ] , 270.0259 ; found , 
 270.0272 .
mp 243244 c ; h nmr ( 500 mhz , acetone - d6 )  
 8.178.15 ( m , 1h ) , 8.04 ( d , j = 7.0 hz , 2h ) , 
 7.01 ( d , j = 4.0 hz , 1h ) , 7.65 ( d , j = 7.0 hz , 1h ) , 7.627.58 ( m , 3h ) , 7.327.30 ( m , 1h ) , 
 7.04 ( br s , 1h ) ; c nmr ( 125.8 mhz , acetone - d6 )  147.5 , 146.3 , 134.9 , 132.2 , 131.5 , 131.5 , 130.4 , 
 129.5 , 129.3 , 128.4 , 128.0 , 127.3 , 126.3 , 125.7 ; hrms ( tof ms es+ ) m / z calcd . for c14h10no2s2
mp 
 254255 c ; h nmr ( 500 mhz , acetone - d6 )  10.13 ( s , 1h ) , 7.64 ( d , j = 4.0 hz , 1h ) , 7.607.50 ( m , 4h ) , 7.457.32 ( m , 4h ) , 
 7.17 ( d , j = 3.5 hz , 1h ) , 6.98 ( br s , 2h ) , 5.28 ( s , 
 2h ) ; c nmr ( 125.8 mhz , acetone - d6 )  191.0 , 160.5 , 147.3 , 144.7 , 137.7 , 136.4 , 133.9 , 
 131.5 , 129.9 , 129.6 , 129.5 , 129.0 , 128.6 , 122.1 , 113.4 , 71.0 ; hrms 
 ( tof ms es+ ) m / z calcd . for c18h15no4s2na [ m + na ] , 396.0340 ; found , 396.0337 .
mp 235236 
 c ; h nmr ( 500 mhz , acetone - d6 )  8.25 ( s , 1h ) , 8.01 ( dd , j = 8.0 , 
 1.0 hz , 1h ) , 7.95 ( d , j = 7.5 hz , 1h ) , 7.627.57 
 ( m , 2h ) , 7.53 ( dd , j = 4.0 , 1.5 hz , 1h ) , 6.95 ( br 
 s , 2h ) , 3.92 ( s , 3h ) ; c nmr ( 125.8 mhz , acetone - d6 )  166.6 , 148.4 , 145.8 , 134.2 , 132.3 , 
 132.2 , 131.1 , 130.5 , 130.2 , 127.3 , 124.9 , 52.6 ; hrms ( tof ms es+ ) m / z calcd . for c12h10no4s2
mp 191192 
 c ; h nmr ( 500 mhz , acetone - d6 )  7.707.65 ( m , 2h ) , 7.58 ( d , j = 3.5 hz , 1h ) , 7.467.39 ( m , 3h ) , 6.89 ( br s , 2h ) , 4.47 ( s , 
 2h ) , 3.36 ( s , 3h ) ; c nmr ( 125.8 mhz , acetone - d6 )  149.8 , 145.0 , 140.8 , 133.1 , 132.3 , 
 129.2 , 126.8 , 124.0 , 74.4 , 58.3 ; hrms ( tof ms es+ ) m / z calc . for c12h12no3s2
mp 171172 
 c ; h nmr ( 500 mhz , acetone - d6 )  7.70 ( d , j = 7.0 hz , 1h ) , 7.557.45 
 ( m , 2h ) , 7.39 ( dd , j = 8.0 , 2.0 hz , 1h ) , 7.267.22 
 ( m , 1h ) , 7.01 ( br s , 2h ) , 2.51 ( s , 3h ) ; c nmr ( 125.8 
 mhz , acetone - d6 )  147.1 , 145.8 , 
 139.0 , 134.7 , 132.3 , 132.0 , 131.3 , 131.2 , 127.7 , 126.9 , 20.7 ; hrms 
 ( tof ms es+ ) m / z calcd .
for c11h11clno2s2 [ m + h ] , 287.9913 ; found , 287.9912 . obtained as a yellow solid ( 265 mg , 88% ) . 

mp 211212 
 c ; h nmr ( 500 mhz , acetone - d6 )  10.4 ( s , 1h ) , 7.93 ( d , j = 8.0 
 hz , 1h ) , 7.88 ( s , 1h ) , 7.81 ( d , j = 8.0 hz , 1h ) , 
 7.70 ( d , j = 4.0 hz , 1h ) , 7.64 ( d , j = 3.5 hz , 1h ) , 7.03 ( br s , 2h ) ; c nmr ( 125.8 mhz , acetone - d6 )  189.1 , 147.6 , 146.0 , 140.1 , 138.6 , 
 132.7 , 132.2 , 130.9 , 128.1 , 126.9 , 125.7 ; hrms ( tof ms es+ ) m / z calcd . for c11h7clno3s2 [ m  h ] , 
 299.9556 ; found , 299.9566 .
mp 209210 c ; h nmr ( 500 mhz , acetone - d6 )  9.29 ( s , 1h ) , 8.15 ( s , 1h ) , 7.637.58 
 ( m , 2h ) ,
7.447.38 ( m , 3h ) , 6.92 ( br s , 2h ) , 2.13 ( s , 3h ) ; c nmr ( 125.8 mhz , acetone - d6 ) 
  169.3 , 149.9 , 145.1 , 141.4 , 134.3 , 132.2 , 130.5 , 124.0 , 121.5 , 
 120.2 , 117.3 , 24.4 ; hrms ( tof ms es+ ) m / z calcd . for c12h13n2o3s2 [ m + h ] , 297.0374 ; found , 297.0376 .
mp 214215 
 c ; h nmr ( 500 mhz , acetone - d6 )  8.27 ( br s , 1h ) , 7.607.50 ( m , 3h ) , 7.18 
 ( d , j = 7.0 hz , 1h ) , 6.956.90 ( m , 1h ) , 6.79 
 ( br s , 2h ) , 2.36 ( s , 3h ) ; c nmr ( 125.8 mhz , acetone - d6 )  152.0 , 145.7 , 144.7 , 131.6 , 130.3 , 
 126.4 , 126.1 , 124.7 , 121.3 , 121.1 , 16.5 ; hrms ( tof ms es+ ) m / z calcd . for c11h10no3s2
mp 256258 
 c ; h nmr ( 500 mhz , acetone - d6 )  8.05 ( d , j = 9.5 hz , 1h ) , 7.91 
 ( d , j = 8.0 hz , 1h ) , 7.74 ( d , j = 
 3.5 hz , 1h ) , 7.69 ( d , j = 9.0 hz , 1h ) , 7.53 ( d , j = 9.5 hz , 1h ) , 7.497.44 ( m , 1h ) , 7.437.38 
 ( m , 1h ) , 7.09 ( d , j = 4 hz , 1h ) , 6.97 ( br s , 2h ) , 
 3.93 ( br s , 3h ) ; c nmr ( 125.8 mhz , acetone - d6 )  155.5 , 145.7 , 142.5 , 134.0 , 131.6 , 130.5 , 129.1 , 
 129.1 , 128.5 , 127.5 , 124.3 , 124.1 , 115.1 , 113.6 , 56.4 ; hrms ( tof ms 
 es+ ) m / z calcd .
for c15h12no3s2 [ m  h ] , 318.0259 ; found , 318.0258 . obtained as a yellow solid ( 122 mg , 46% ) . 

mp 148150 c ; h nmr ( 500 mhz , acetone - d6 )  
 7.737.67 ( m , 2h ) , 7.607.53 ( m , 3h ) , 7.507.44 
 ( m , 1h ) , 6.92 ( br s , 2h ) , 6.856.75 ( m , 1h ) , 5.91 ( dd , j = 17.5 , 4.5 hz , 1h ) , 5.32 ( dd , j = 11.0 , 
 4.5 hz , 1h ) ; c nmr ( 125.8 mhz , acetone - d6 )  149.6 , 145.2 , 139.2 , 137.1 , 133.3 , 132.3 , 128.0 , 
 127.1 , 124.1 , 115.3 ; hrms ( tof ms es+ ) m / z calcd . for c12h10no2s2 [ m  h ] , 264.0153 ; found , 264.0163 .
mp 188190 c ; h nmr ( 500 mhz , acetone - d6 )  7.687.50 ( m , 5h ) , 7.42 ( d , j = 4 hz , 1h ) , 6.90 ( br s , 2h ) , 1.36 ( s , 9h ) ; c nmr ( 125.8 mhz , acetone - d6 )  152.8 , 149.9 , 144.4 , 
 132.1 , 130.9 , 126.9 , 126.5 , 123.4 , 35.1 , 31.7 , 31.3 ; hrms ( tof ms 
 es+ ) m / z calcd . for c14h16no2s2 [ m  h ] , 294.0622 ; found , 294.0624 .
mp 196198 
 c ; h nmr ( 500 mhz , acetone - d6 )  8.47 ( s , 1h ) , 8.27 ( s , 1h ) , 8.23 ( s , 1h ) , 7.74 ( d , j = 4.0 hz , 1h ) , 7.66 ( d , j = 4.0 hz , 1h ) , 
 7.02 ( br s , 2h ) , 3.99 ( s , 3h ) ; c nmr ( 125.8 mhz , acetone - d6 )  165.4 , 147.1 , 146.2 , 135.6 , 133.3 , 
 132.5 , 132.2 , 130.8 , 127.3 , 126.4 , 126.3 , 53.1 ; hrms ( tof ms es+ ) m / z calc . for c12h10n2o2s2
mp 
 155156 c ; h nmr ( 500 mhz , acetone - d6 )  
 7.63 ( dd , j = 7.0 , 2.0 hz , 2h ) , 7.54 ( d , j = 4.0 hz , 1h ) , 7.31 ( d , j = 4.0 hz , 1h ) , 
 7.01 ( dd , j = 7.0 , 2.0 hz , 2h ) , 6.85 ( br s , 2h ) , 
 4.154.06 ( m , 2h ) , 1.421.35 ( m , 3h ) ; c 
 nmr ( 125.8 mhz , acetone - d6 )  160.7 , 
 150.2 , 143.7 , 132.3 , 128.2 , 126.2 , 122.7 , 115.9 , 64.3 , 15.0 ; hrms 
 ( tof ms es+ ) m / z calcd . for c12h12no3s2
mp 262264 
 c ; h nmr ( 500 mhz , acetone - d6 )  7.89 ( dd , j = 7.5 , 1.5 hz , 1h ) , 
 7.687.60 ( m , 4h ) , 7.517.46 ( m , 2h ) , 7.457.39 
 ( m , 2h ) , 7.32 ( d , j = 6.5 hz , 1h ) , 7.177.11 
 ( m , 1h ) , 6.90 ( br s , 2h ) , 5.45 ( s , 2h ) ; c nmr ( 125.8 
 mhz , acetone - d6 )  155.4 , 145.3 , 
 144.9 , 137.6 , 130.6 , 129.3 , 129.1 , 128.8 , 128.4 , 125.4 , 122.7 , 122.1 , 
 114.3 , 71.1 ; hrms ( tof ms es+ ) m / z calcd . for c17h15no3s2na [ m + na ] , 368.0391 ;
mp 144145 
 c ; h nmr ( 500 mhz , acetone - d6 )  7.61 ( d , j = 3.5 hz , 1h ) , 7.41 
 ( d , j = 7.5 hz , 1h ) , 7.34 ( d , j = 
 4.5 hz , 2h ) , 7.307.26 ( m , 1h ) , 7.14 ( d , j = 4.0 hz , 1h ) , 6.91 ( br s , 2h ) , 2.41 ( s , 3h ) ; c nmr 
 ( 125.8 mhz , acetone - d6 )  148.8 , 
 145.7 , 136.9 , 133.4 , 131.9 , 131.3 , 131.0 , 129.8 , 127.5 , 127.2 , 21.1 ; 
 hrms ( tof ms es+ ) m / z calcd . for 
 c11h12no2s2
mp 256258 c ; h nmr ( 500 mhz , acetone - d6 )  
 7.697.65 ( m , 2h ) , 7.60 ( dd , j = 7.5 , 1.5 
 hz , 1h ) , 7.53 ( dd , j = 7.5 , 1.5 hz , 2h ) , 7.44 ( t , j = 7.5 hz , 1h ) , 7.39 ( td , j = 7.5 , 1.5 
 hz , 1h ) , 7.35 ( dd , j = 7.5 , 1.5 hz , 1h ) , 7.33 ( d , j = 3.5 hz , 1h ) ; c nmr ( 125.8 mhz , acetone - d6 )  147.0 , 146.0 , 137.1 , 136.6 , 136.1 , 
 135.7 , 134.1 , 131.1 , 130.9 , 130.4 , 129.7 , 129.4 , 129.3 , 129.0 , 128.7 ; 
 hrms ( tof ms es+ ) m / z calcd . for 
 c16h10no2s4 [ m  
 h ] , 375.9594 ; found , 375.9606 . obtained as a yellow solid ( 268 mg , 90% ) . 

mp 208209 
 c ; h nmr ( 500 mhz , acetone - d6 )  10.06 ( s , 1h ) , 8.01 ( d , j = 9.0 
 hz , 1h ) , 7.68 ( d , j = 3.5 hz , 1h ) , 7.29 ( d , j = 4.0 hz , 1h ) , 7.23 ( dd , j = 9.0 , 2.5 
 hz , 1h ) , 7.13 ( d , j = 2.0 hz , 1h ) , 7.03 ( br s , 2h ) , 
 4.02 ( s , 3h ) ; c nmr ( 125.8 mhz , acetone - d6 )  189.7 , 164.7 , 147.8 , 144.5 , 139.2 , 131.4 , 130.2 , 
 130.2 , 128.7 , 116.9 , 116.4 , 59.5 ; hrms ( tof ms es+ ) m / z calcd . for c12h11no4s2na [ m + na ]
mp 144146 
 c ; h nmr ( 500 mhz , acetone - d6 )  7.47 ( d , j = 3.5 hz , 1h ) , 7.02 
 ( d , j = 3.5 hz , 1h ) , 6.80 ( br s , 2h ) , 6.33 ( m , 1h ) , 
 2.432.41 ( m , 2h ) , 2.242.08 ( m , 2h ) , 1.821.75 
 ( m , 2h ) , 1.701.62 ( m , 2h ) ; c nmr ( 125.8 mhz , 
 acetone - d6 )  152.4 , 142.6 , 131.4 , 
 131.4 , 127.3 , 121.8 , 27.7 , 26.1 , 23.1 , 22.4 ; hrms ( tof ms es+ ) m / z calcd . for c10h13no2s2 na [ m + na ] , 266.0285 ; found , 
 266.0287 .
mp 
 155156 c ; h nmr ( 500 mhz , acetone - d6 )  
 7.427.37
( m , 1h ) , 6.856.81 ( m , 1h ) , 6.73 ( br s , 2h ) , 
 2.86 ( d , j = 7.5 hz , 1h ) , 1.161.108 ( m , 2h ) , 
 0.840.74 ( m , 2h ) ; c nmr ( 125.8 mhz , acetone - d6 )  155.8 , 142.2 , 131.4 , 123.4 , 12.1 , 
 11.1 ; hrms ( tof ms es+ ) m / z calcd . 
 for c7h8no2s2 [ m + h ] , 204.0153 ;
mp 
 212214 c ; h nmr ( 500 mhz , acetone - d6 )  10.36 ( s , 1h ) , 7.907.71 ( m , 
 4h ) , 7.11 ( br s , 2h ) ; c nmr ( 125.8 mhz , acetone - d6 )  186.4 , 154.6 , 152.5 , 149.3 , 149.2 , 
 147.3 , 147.2 , 139.6 , 131.7 , 129.5 , 129.5 , 124.8 , 124.4 ; hrms ( tof 
 ms es+ ) m / z calcd .
for c11h6f2no3s2 [ m  
 h ] , 301.9757 ; found , 301.9757 . obtained as a yellow solid ( 273 mg , 94% ) . 
 mp 236237 c ; h nmr ( 500 mhz , acetone - d6 )  
 9.40 ( s , 1h ) , 8.618.59 ( m , 1h ) , 8.24 ( d , j = 8.0 hz , 1h ) , 8.00 ( d , j = 5.5 hz , 1h ) , 7.92 ( dd , j = 7.5 , 1.5 hz , 1h ) , 7.807.73 ( m , 2h ) , 7.417.39 
 ( m , 1h ) , 7.06 ( br s , 2h ) ; c nmr ( 125.8 mhz , acetone - d6 )  154.0 , 147.0 , 145.7 , 145.3 , 134.5 , 
 133.2 , 131.7 , 130.6 , 130.1 , 129.9 , 128.8 , 127.9 , 118.2 ; hrms ( tof 
 ms es+ ) m / z calcd . for c13h11n2o2s2 [ m + h ] , 291.0262 ; found , 291.0260 .
mp 194195 
 c ; h nmr ( 500 mhz , acetone - d6 )  8.478.45 ( m , 1h ) , 8.148.11 ( m , 1h ) , 
 7.657.63 ( m , 1h ) , 7.567.52 ( m , 1h ) , 7.527.49 
 ( m , 1h ) , 7.04 ( br s , 1h ) ; c nmr ( 125.8 mhz , acetone - d6 )  150.2 , 149.0 , 147.7 , 143.2 , 140.7 , 
 130.9 , 129.4 , 129.3 , 124.1 ; hrms ( tof ms es+ ) m / z calcd . for c9h8cln2o2s2 [ m + h ] , 274.9714 ; found , 274.9709 . obtained as a yellow solid ( 223 mg , 78% ) .
mp 202203 
 c ; h nmr ( 500 mhz , acetone - d6 )  9.02 ( d , j = 1.5 hz , 1h ) , 8.608.53 
 ( m , 1h ) , 8.458.36 ( m , 1h ) , 7.84 ( d , j = 6.5 
 hz , 1h ) , 7.71 ( d , j = 6.5 hz , 1h ) , 7.12 ( br s , 2h ) ; c nmr ( 125.8 mhz , acetone - d6 ) 
  157.1 , 148.7 , 146.5 , 143.1 , 137.8 , 135.3 , 132.4 , 128.1 , 119.5 ; 
 hrms ( tof ms es+ ) m / z calcd .
for 
 c9h8n3o4s2 [ m 
 + h ] , 285.9956 ; found , 285.9955 . obtained as a yellow solid ( 213 mg , 78% ) . 

mp 
 166167 c ; h nmr ( 500 mhz , acetone - d6 )  10.06 ( s , 1h ) , 8.59 ( d , j = 5.0 hz , 1h ) , 7.85 ( d , j = 5.0 hz , 1h ) , 7.61 ( dd , j = 8.5 , 3.8 hz , 1h ) , 7.41 ( dd , j = 8.5 , 
 4.0 hz , 1h ) , 6.96 ( br s , 2h ) ; c nmr ( 125.8 mhz , acetone - d6 )  185.6 , 146.0 , 141.5 , 140.3 , 139.9 , 
 133.7 , 131.3 , 128.9 , 128.2 ; hrms ( tof ms es+ ) m / z calcd . for c9h7no3s3na [ m + na ] , 295.9486 ; found , 295.9491 .
mp 214215 
 c ; h nmr ( 500 mhz , acetone - d6 )  7.64 ( d , j = 3.5 hz , 1h ) , 7.20 
 ( d , j = 4.0 hz , 1h ) , 6.96 ( br s , 2h ) , 2.55 ( s , 3h ) , 
 2.35 ( s , 3h ) ; c nmr ( 125.8 mhz , acetone - d6 )  167.3 , 158.4 , 145.3 , 137.1 , 131.3 , 126.9 , 109.9 , 
 11.8 , 10.8 ; hrms ( tof ms es+ ) m / z calcd . for c9h10n2o3s2na [ m + na ] , 281.0031 ; found , 281.0027 .
mp 188189 c ; h nmr ( 500 mhz , dmso - d6 )  
 7.74 ( br s , 2h ) , 7.64 ( d , j = 5.5 hz , 1h ) , 7.48 ( d , j = 2.1 hz , 1h ) , 7.46 ( dd , j = 3.5 , 1.0 
 hz , 1h ) , 7.31 ( d , j = 4.0 hz , 1h ) , 7.15 ( t , j = 4.0 hz , 1h ) ; c nmr ( 125.8 mhz , dmso - d6 )  143.4 , 140.9 , 134.7 , 131.0 , 128.7 , 
 127.3 , 125.9 , 123.7 ; hrms ( tof ms es+ ) m / z calcd . for c8h8no2s3 [ m + h ] , 245.9717 ; found , 245.9712 .
mp 181182 c ; h nmr ( 500 mhz , acetone - d6 )  
 7.817.79 ( m , 1h ) , 7.62 ( dd , j = 5.0 , 3.0 
 hz , 1h ) , 5.54 ( d , j = 4.0 hz , 1h ) , 7.46 ( dd , j = 5.0 , 1.0 hz , 1h ) ; c nmr ( 125.8 mhz , acetone - d6 )  144.8 , 144.0 , 135.1 , 132.1 , 128.4 , 
 126.7 , 124.0 , 122.7 ; hrms ( tof ms es+ ) m / z calcd . for c8h6no2s3 [ m  h ] , 243.9561 ; found , 243.9572 . obtained as a white solid ( 190 mg , 79% ) .
mp 200201 c ; h nmr ( 500 mhz , acetone - d6 )  
 8.94 ( d , j = 2.0 hz , 1h ) , 8.60 ( d , j = 3.0 hz , 1h ) , 8.108.05 ( m , 1h ) , 7.63 ( d , j = 3.5 hz , 1h ) , 7.57 ( d , j = 4.0 hz , 1h ) , 7.507.46 
 ( m , 1h ) , 6.99 ( br s , 2h ) ; c nmr ( 125.8 mhz , acetone - d6 )  150.8 , 147.8 , 146.5 , 146.1 , 134.1 , 
 132.3 , 130.0 , 125.5 , 125.0 ; hrms ( tof ms es+ ) m / z calcd . for c9h9n2o2s2 [ m + h ] , 241.0105 ; found , 241.0107 . obtained as a yellow solid ( 326 mg , 78% ) . 

mp 246248 c ; h nmr ( 500 mhz , acetone - d6 )  8.20 ( s , 1h ) , 8.13 ( d , j = 7.0 hz , 1h ) , 7.92 ( d , j = 7.5 hz , 1h ) , 7.70 ( t , j = 6.5 hz , 1h ) , 7.65 ( d , j = 4.0 hz , 1h ) , 
 7.637.59 ( m , 2h ) , 7.53 ( d , j = 4.0 hz , 1h ) , 
 7.48 ( t , j = 8.0 hz , 1h ) , 7.437.39 ( m , 1h ) ; c nmr ( 125.8 mhz , acetone - d6 ) 
  144.7 , 140.3 , 138.4 , 136.1 , 135.4 , 131.8 , 130.5 , 128.7 , 127.9 , 
 126.5 , 125.6 , 125.1 , 121.1 , 116.8 , 114.6 ; hrms ( tof ms es+ ) m / z calcd . for c18h13n2o4s3 [ m  h ] , 417.0037 ; found , 417.0036 . obtained as a yellow solid ( 159 mg , 58% ) . 

mp 196197 
 c ; h nmr ( 500 mhz , dmso - d6 )  8.81 ( d , j = 2.5 hz , 1h ) , 8.20 ( dd , j = 8.5 , 2.5 hz , 1h ) , 7.82 ( br s , 2h ) , 7.69 ( d , j = 3.5 hz , 1h ) , 7.63 ( dd , j = 8.0 , 4.5 
 hz , 1h ) , 7.59 ( d , j = 4.0 hz , 1h ) ; c 
 nmr ( 125.8 mhz , dmso - d6 )  150.0 , 
 146.7 , 145.8 , 142.4 , 136.8 , 131.0 , 128.1 , 125.7 , 124.7 ; hrms ( tof 
 ms es+ ) m / z calcd . for c9h8cln2o2s2
mp 188189 c ; h nmr ( 500 mhz , acetone - d6 )  9.92 ( s , 1h ) , 7.85 ( s , 1h ) , 7.64 
 ( d , j = 7.0 hz , 1h ) , 7.43 ( d , j = 
 4.0 hz , 1h ) , 7.02 ( br s , 2h ) , 2.80 ( s , 3h ) ; c nmr ( 125.8 
 mhz , acetone - d6 )  183.9 , 147.5 , 
 142.5 , 141.7 , 140.6 , 139.1 , 137.9 , 131.9 , 128.1 , 15.8 ; hrms ( tof ms 
 es+ ) m / z calcd . for c10h10no3s3 [ m + h ] , 285.9666 ; 
 found , 285.9673 .
mp 248250 
 c ; h nmr ( 500 mhz , dmso - d6 )  8.48 ( dd , j = 8.0 , 1.0 hz , 1h ) , 8.478.44 
 ( m , 1h ) , 8.138.10 ( m , 1h ) , 7.86 ( s , 2h ) , 7.85 ( d , j = 7.5 hz , 1h ) , 7.727.69 ( m , 2h ) , 7.67 ( t , j = 7.5 hz , 1h ) , 7.627.57 ( m , 2h ) ; c nmr ( 125.8 mhz , dsmo - d6 )  145.4 , 
 145.2 , 138.1 , 136.5 , 136.4 , 134.9 , 130.7 , 127.7 , 127.6 , 126.9 , 126.1 , 
 125.8 , 125.3 , 123.0 , 122.6 , 122.4 ; hrms ( tof ms es+ ) m / z calcd . for c16h12no2s3 [ m + h ] , 346.0030 ; found , 346.0036 .
mp 
 156158 c ; h nmr ( 500 mhz , dmso - d6 )  9.93 ( s , 1h ) , 8.04 ( d , j = 
 4.0 hz , 1h ) , 7.86 ( br s , 2h ) , 7.68 ( d , j = 4.0 hz , 
 1h ) , 7.59 ( d ,
j = 3.5 hz , 1h ) , 7.56 ( d , j = 4.0 hz , 1h ) ; c nmr ( 125.8 mhz , dmso - d6 )  184.2 , 146.1 , 143.3 , 142.7 , 139.1 , 139.0 , 131.1 , 
 127.0 , 126.6 ; hrms ( tof ms es ) m / z calcd . for c9h5no3s3 [ m  h ] , 271.9510 ; found , 271.9512 .
mp 209210 
 c ; h nmr ( 500 mhz , dmso - d6 )  7.90 ( br s , 1h ) , 7.68 ( br s , 2h ) , 7.537.49 ( m , 
 1h ) , 7.487.46 ( m , 1h ) , 7.447.38 ( m , 3h ) , 6.51 ( s , 
 1h ) ; c nmr ( 125.8 mhz , dmso - d6 )  150.5 , 142.1 , 136.2 , 131.1 , 128.1 , 126.9 , 123.6 , 121.6 , 
 119.5 , 117.7 , 112.3 , 101.8 ; hrms ( tof ms es+ ) m / z calcd . for c12h9n2 [ m 
  o2s2 ] , 277.0112 ; 
 found , 277.0117 . obtained as a blackish brown solid ( 188 mg , 82% ) . 

mp 165167 
 c ; h nmr ( 500 mhz , acetone - d6 )  7.687.66 ( m , 1h ) , 7.54 ( d , j = 3.5 hz , 1h ) , 7.32 ( d , j = 4.0 hz , 1h ) , 6.94 ( br 
 s , 2h ) , 6.88 ( d , j = 3.5 hz , 1h ) ,
6.616.59 
 ( m , 1h ) ; c nmr ( 125.8 mhz , acetone - d6 )  148.5 , 144.1 , 138.7 , 131.9 , 127.8 , 122.8 , 113.1 , 
 108.3 ; hrms ( tof ms es+ ) m / z calcd . 
 for c8h8no3s2 [ m + h ] , 229.9946 ;
mp 186187 c ; h nmr ( 500 mhz , acetone - d6 )  
 8.048.01 ( m , 1h ) , 7.677.63 ( m , 1h ) , 7.537.49 
 ( m , 1h ) ,
7.237.19 ( m , 1h ) , 6.87 ( br s , 2h ) , 6.80 ( s , 1h ) ; c nmr ( 125.8 mhz , acetone - d6 ) 
  145.2 , 143.5 , 140.4 , 131.7 , 129.3 , 124.0 , 120.2 , 109.6 ; hrms 
 ( tof ms es+ ) m / z calcd . for c8h6no3s2 [ m  h ] , 227.9789 ; found , 227.9781 .
mp 192193 
 c ; h nmr ( 500 mhz , acetone - d6 )  7.52 ( d , j = 4.0 hz , 1h ) , 7.21 
 ( d , j = 4.0 hz , 1h ) , 6.88 ( br s , 2h ) , 6.71 ( d , j = 3.5 hz , 1h ) , 6.196.17 ( m , 1h ) , 2.33 ( s , 3h ) ; c nmr ( 125.8 mhz , acetone - d6 ) 
  153.6 , 146.6 , 142.8 , 139.0 , 131.7 , 121.5 , 109.1 , 109.0 , 13.1 ; 
 hrms ( tof ms es ) m / z calcd . 

 a mild , practical protocol has been 
 developed for the suzuki cross - coupling 
 of unprotected thienylsulfonamides from air- and bench - stable organotrifluoroborates 
 in the absence of a protecting group on the sulfonamide nitrogen . 
 
 the developed synthetic method can be applied to the preparation of 
 various arylated and heteroarylated thienylsulfonamides under conditions 
 that are tolerant of a broad range of functional groups . 
Experimental Section