to a 2 dram , clear glass 
 vial equipped 
 with a teflon - coated magnetic stir bar were added 4,4-di - tert - butyl-2,2-bipyridine ( 13.4 mg , 0.050 mmol ) 
 and [ nicl2(dme ) ] ( 11 mg , 0.050 mmol ) . the vial was sealed 
 and evacuated three times via an inlet needle and purged with argon . the resulting suspension 
 was heated briefly with a heat gun until the nickel and ligand were 
 fully solubilized , yielding a pale green solution . solvents were then 
 evaporated in vacuo to give a fine coating of the ligated nickel complex . once dry , a phenol derivative ( 134 mg , 0.5 mmol , 1.0 equiv ) ( liquid 
 phenol derivatives were added with solvent ) , alkylsilicate ( 335 mg , 
 0.75 mmol , 1.5 equiv ) , and [ ru(bpy)3]2pf6 ( 8.6 mg , 0.01 mmol ) were added in succession . under an inert 
 atmosphere , dmf ( 5 ml ) the cap was sealed with parafilm , 
 and the solution was irradiated in front of a 26 w cfl bulb or blue 
 leds . the temperature of the reaction was maintained at approximately 
 27 c via a fan . once judged to be complete , the solution was transferred to a separatory 
 funnel and diluted with deionized h2o ( 20 ml ) and 
 et2o ( 20 ml ) . the layers were separated , and the 
 aqueous layer was extracted with et2o ( 3  20 
 ml ) . the combined organic layers were washed with 1 m naoh ( 30 
 ml ) , 1 m hcl ( 30 ml ) , and brine ( 50 ml ) . the organic 
 layer was dried ( mgso4 ) , and the solvent was removed in vacuo by rotary evaporation . further purification was 
 accomplished via column chromatography , eluting with hexane / etoac 
 to give the desired compound as a light yellow oil ( 102 mg , 95% ) . h nmr ( cdcl3 , 500 mhz ) :  7.89 ( d , j = 8.3 hz , 2h ) , 7.28 ( d , j = 8.3 hz , 2h ) , 
 4.09 ( t , j = 6.5 hz , 2h ) , 2.75 ( t , j = 7.6 hz , 2h ) , 2.59 ( s , 3h ) , 2.05 ( s , 3h ) , 2.021.93 ( m , 
 2h ) . c { h } nmr ( cdcl3 , 125 mhz ) : 
  197.8 , 171.2 , 147.1 , 135.4 , 128.7 , 128.7 , 63.7 , 32.4 , 29.9 , 
 26.7 , 21.0 . obtained as a colorless 
 oil ( 104 mg , 
 94% ) . h nmr ( cdcl3 , 500 mhz ) :  8.02 
 ( d , j = 8.1 hz , 1h ) , 7.85 ( d , j = 
 7.9 hz , 1h ) , 7.72 ( d , j = 7.9 hz , 1h ) , 7.557.44 
 ( m , 2h ) , 7.39 ( t , j = 7.3 hz , 1h ) , 7.32 ( d , j = 7.0 hz , 1h ) , 4.16 ( t , j = 6.5 hz , 2h ) , 
 3.15 ( t , j = 7.7 hz , 2h ) , 2.152.03 ( m , 5h ) . c { h } nmr ( cdcl3 , 125 mhz ) :  
 171.2 , 137.3 , 134.0 , 131.9 , 128.9 , 127.0 , 126.1 , 126.0 , 125.6 , 125.6 , 
 123.7 , 64.2 , 29.6 , 29.4 , 21.1 . obtained 
 as a colorless oil ( 57 mg , 
 50% ) . 7.837.74 
 ( m , 3h ) , 7.62 ( s , 1h ) , 7.487.38 ( m , 2h ) , 7.32 ( dd , j = 8.4 , 1.8 hz , 1h ) , 4.13 ( t , j = 6.6 
 hz , 2h ) , 2.85 ( t , j = 7.6 hz , 2h ) , 2.092.01 
 ( m , 5h ) . c { h } nmr ( cdcl3 , 125 
 mhz ) :  171.2 , 138.8 , 133.7 , 132.2 , 128.1 , 127.7 , 127.5 , 127.2 , 
 126.6 , 126.1 , 125.3 , 64.0 , 32.5 , 30.2 , 21.1 . obtained 
 as a colorless oil ( 31 mg , 30% ) . h nmr ( cdcl3 , 500 mhz ) :  7.58 ( d , j = 7.3 hz , 2h ) , 7.27 
 ( d , j = 7.7 hz , 2h ) , 4.09 ( t , j = 
 6.2 hz , 2h ) , 2.75 ( t , j = 7.7 hz , 2h ) , 2.04 ( s , 3h ) , 
 2.041.93 ( m , 2h ) . c { h } nmr ( cdcl3 , 125 mhz ) :  171.3 , 146.9 , 132.4 , 129.3 , 119.0 , 110.2 , 
 63.5 , 32.5 , 29.8 , 21.0 . ir ( neat ) :  = 2957 , 2227 , 1734 , 1608 , 
 1505 , 1453 , 1415 , 1387 , 1366 , 1234 , 1178 , 1038 , 915 , 878 , 846 , 815 , 
 733 , 633 , 606 , 559 cm . hrms ( esi ) : m / z calcd for c12h13no2na [ m + na ] 226.0844 , found 226.0834 . obtained 
 as a colorless 
 oil ( 61 mg , 42% ) . h nmr ( cdcl3 , 500 mhz ) :  
 7.56 ( d , j = 8.0 hz , 2h ) , 7.31 ( d , j = 7.9 hz , 2h ) , 4.10 ( t , j = 6.5 hz , 2h ) , 2.76 ( t , j = 7.8 hz , 2h ) , 2.06 ( s , 3h ) , 2.031.95 ( m , 2h ) . c { h } nmr ( cdcl3 , 125 mhz ) :  
 171.2 , 145.4 , 128.8 , 128.6 ( q , j = 32.3 hz ) , 125.5 
 ( q , j = 3.8 hz ) , 122.3 ( q , j = 271.9 
 hz ) , 63.7 , 32.2 , 30.0 , 21.1 . h nmr ( cdcl3 , 500 mhz ) :  7.497.34 
 ( m , 4h ) , 
 4.10 ( t , j = 6.5 hz , 2h ) , 2.75 ( t , j = 7.5 hz , 2h ) , 2.05 ( s , 3h ) , 2.031.93 ( m , 2h ) . c { 1h } nmr ( cdcl3 , 125 mhz ) :  171.2 , 142.2 , 131.9 , 
 129.0 , 130.9 ( q , j = 32.0 hz ) , 125.2 ( q , j = 3.7 hz ) , 124.3 ( q , j = 272.2 hz ) , 123.1 
 ( q , j = 3.9 hz ) , 63.7 , 32.2 , 30.1 , 21.0 . ir ( neat ) :  
 = 1737 , 1450 , 1388 , 1367 , 1328 , 1236 , 1199 , 1161 , 1120 , 1072 , 1039 , 
 1002 , 951 , 904 , 799 , 733 , 702 , 661 , 631 , 606 cm . hrms ( esi ) : m / z calcd for c12h13f3o2na [ m + na ] 269.0765 , found 269.0754 . obtained 
 as a white solid ( 63 mg , 63% ) ; 
 mp , 5758 c . h nmr ( cdcl3 , 500 
 mhz ) :  7.89 ( d , j = 8.3 hz , 2h ) , 7.29 ( d , j = 8.2 hz , 2h ) , 2.58 ( m , 4h ) , 1.921.81 ( m , 4h ) , 
 1.801.72 ( m , 1h ) , 1.501.34 ( m , 4h ) , 1.331.18 
 ( m , 1h ) . c { h } nmr ( cdcl3 , 125 
 mhz ) :  197.9 , 153.8 , 135.2 , 128.6 , 127.1 , 44.8 , 34.2 , 26.8 , 
 26.6 , 26.1 . obtained as a yellow oil ( 92 mg , 92% ) . h nmr ( cdcl3 , 500 mhz ) :  7.87 ( d , j = 8.5 hz , 2h ) , 7.30 ( d , j = 8.3 hz , 2h ) , 
 2.832.75 ( m , 1h ) , 2.57 ( s , 3h ) , 2.422.34 ( m , 2h ) , 
 1.841.70 ( m , 1h ) , 1.691.48 ( m , 3h ) , 1.411.34 
 ( m , 1h ) , 1.331.18 ( m , 3h ) . c { h } 
 nmr ( cdcl3 , 125 mhz ) :  197.9 , 153.5 , 134.8 , 128.5 , 
 127.3 , 47.6 , 42.8 , 39.2 , 37.0 , 36.3 , 30.7 , 28.9 , 26.6 . ir ( neat ) : 
  = 2949 , 2869 , 1679 , 1604 , 1568 , 1454 , 1411 , 1357 , 1308 , 1267 , 
 1212 , 1185 , 1139 , 1014 , 955 , 848 , 822 , 605 , 591 , 570 cm . hrms ( esi ) : m / z calcd for c15h19o [ m + h ] 215.1436 , found 215.1436 . obtained as a colorless oil ( 76 mg , 74% ) . h 
 nmr ( cdcl3 , 500 mhz ) :  7.88 ( d , j = 8.3 hz , 2h ) , 7.27 ( d , j = 8.2 hz , 2h ) , 
 2.692.62 ( t , j = 7.7 hz , 2h ) , 2.58 ( s , 3h ) , 
 1.671.58 ( m , 2h ) , 1.381.24 ( m , 6h ) , 0.920.82 
 ( m , 3h ) . c { h } nmr ( cdcl3 , 125 
 mhz ) :  197.9 , 148.9 , 135.0 , 128.7 , 128.5 , 36.1 , 31.8 , 31.2 , 
 29.0 , 26.6 , 22.7 , 14.2 . obtained as a colorless 
 oil ( 69 mg , 78% ) . h nmr ( cdcl3 , 500 mhz ) :  
 7.87 ( d , j = 8.2 hz , 2h ) , 7.23 ( d , j = 8.3 hz , 2h ) , 
 2.58 ( s , 3h ) , 2.53 ( d , j = 7.2 hz , 2h ) , 1.90 ( m , 
 1h ) , 0.91 ( d , j = 6.6 hz , 6h ) . c { h } nmr ( cdcl3 , 125 mhz ) :  198.0 , 147.7 , 
 135.1 , 129.4 , 128.4 , 45.5 , 30.2 , 26.6 , 22.4 . obtained as a light yellow oil ( 62 mg , 
 55% ) . h nmr ( cdcl3 , 500 mhz ) :  7.88 
 ( d , j = 8.1 hz , 2h ) , 7.27 ( d , j = 
 8.1 hz , 2h ) , 5.715.62 ( m , 2h ) , 2.71 ( t , j = 7.8 hz , 2h ) , 2.58 ( s , 3h ) , 2.201.99 ( m , 3h ) , c { h } 
 nmr ( cdcl3 , 125 mhz ) :  197.9 , 148.9 , 135.1 , 128.7 , 
 128.6 , 127.2 , 126.4 , 38.2 , 33.4 , 33.2 , 31.9 , 28.9 , 26.6 , 25.2 . ir 
 ( neat ) :  = 3021 , 2912 , 2836 , 1680 , 1605 , 1433 , 1412 , 1356 , 
 1302 , 1265 , 1181 , 1017 , 954 , 871 , 847 , 818 , 689 , 653 , 596 , 581 cm . hrms ( esi ) : m / z calcd for c16h21o [ m + h ] 229.1592 , 
 found 229.1590 . obtained as a colorless oil ( 72 mg , 75% ) . h nmr ( cdcl3 , 500 mhz ) :  7.89 ( d , j = 8.2 hz , 2h ) , 7.28 ( d , j = 8.2 hz , 2h ) , 
 3.38 ( t , j = 6.3 hz , 2h ) , 3.34 ( s , 3h ) , 2.75 ( t , j = 7.8 hz , 2h ) , 2.58 ( s , 3h ) , 1.951.85 ( m , 2h ) . c { h } nmr ( cdcl3 , 125 mhz ) :  
 197.9 , 
 147.9 , 135.2 , 128.8 , 128.6 , 71.7 , 58.7 , 32.4 , 31.0 , 26.6 . ir ( neat ) : 
  = 2926 , 2867 , 1679 , 1606 , 1430 , 1412 , 1386 , 1357 , 1266 , 1207 , 
 1181 , 1115 , 1073 , 1017 , 955 , 886 , 845 , 814 , 597 , 584 cm . hrms ( esi ) : m / z calcd for c12h17o2 [ m + h ] 193.1229 , 
 found 193.1231 . obtained as a colorless oil ( 86 mg , 57% ) . h nmr ( cdcl3 , 500 mhz ) :  9.35 ( br s , 1h ) , 
 7.88 ( d , j = 8.3 hz , 2h ) , 7.29 ( d , j = 8.2 hz , 2h ) , 4.033.93 ( m , 2h ) , 3.32 ( q , j = 5.7 hz , 2h ) , 2.772.66 ( m , 4h ) , 2.58 ( s , 3h ) , 1.961.86 
 ( m , 2h ) , 1.811.67 ( m , 6h ) . c { h } 
 nmr ( cdcl3 , 125 mhz ) :  197.9 , 179.6 , 155.0 , 147.4 , 
 135.2 , 128.7 , 128.7 , 43.9 , 40.0 , 39.9 , 33.3 , 30.8 , 29.2 , 28.4 , 26.7 , 
 23.6 . ir ( neat ) :  = 1695 , 1680 , 1651 , 1606 , 1526 , 1453 , 1435 , 
 1397 , 1358 , 1333 , 1267 , 1213 , 1179 , 1163 , 1082 , 969 , 844 , 729 , 645 , 
 595 cm . hrms ( esi ) : m / z calcd for c18h25n2o3 [ m + h ] 317.1865 , found 317.1877 . obtained 
 as a yellow semisolid ( 69 mg , 63% ) . h nmr ( cdcl3 , 500 mhz ) : 8.11 ( d , j = 8.5 , 1h ) , 7.84 ( d , j = 7.8 , 1h ) , 7.68 ( d , j = 8.0 , 1h ) , 7.527.35 
 ( m , 4h ) , 3.343.30 
 ( m , 1h ) , 2.101.80 ( m , 5h ) , 1.751.49 ( m , 4h ) , 1.401.28 
 ( m , 1h ) . c { h } nmr ( cdcl3 , 125 
 mhz ) :  143.9 , 134.0 , 131.5 , 129.0 , 126.3 , 125.8 , 125.7 , 125.3 , 
 123.3 , 122.4 , 39.4 , 34.3 , 27.4 , 26.7 . obtained as a colorless oil ( 80 mg , 72% ) . h nmr ( cdcl3 , 500 mhz ) :  8.09 ( d , j = 8.3 hz , 1h ) , 7.83 ( d , j = 8.0 hz , 1h ) , 
 7.67 ( d , j = 7.5 hz , 1h ) , 7.537.43 ( m , 2h ) , 
 7.437.34 
 ( m , 2h ) , 3.433.32 ( m , 1h ) , 2.59 ( d , j = 3.5 
 hz , 1h ) , 2.38 ( s , 1h ) , 2.021.94 ( m , 1 h ) , 1.791.58 
 ( m , 4h ) , 1.571.22 ( m , 3h ) . c { h } 
 nmr ( cdcl3 , 125 mhz ) :  143.2 , 134.2 , 132.1 , 128.9 , 
 126.1 , 125.6 , 125.5 , 125.4 , 124.4 , 121.7 , 43.4 , 41.7 , 39.7 , 37.1 , 
 36.7 , 30.6 , 29.4 . ir ( neat ) :  = 2948 , 2868 , 1739 , 1596 , 1509 , 
 1452 , 1396 , 1372 , 1311 , 1297 , 1239 , 1139 , 1045 , 950 , 907 , 793 , 775 , 
 731 , 648 , 560 cm . hrms ( esi ) : m / z calcd for c17h18 [ m ] 222.1409 , found 222.1414 . obtained as a yellow oil ( 167 mg , 
 97% ) . h nmr ( cdcl3 , 500 mhz ) :  7.26 
 ( d , j = 8.6 hz , 2h ) , 7.19 ( d , j = 
 8.6 hz , 2h ) , 4.09 ( t , j = 6.4 hz , 2h ) , 2.72 ( t , j = 7.6 hz , 2h ) , 2.05 ( s , 3h ) , 2.001.92 ( m , 2h ) . c { h } nmr ( cdcl3 , 125 mhz ) :  
 171.2 , 148.0 , 141.9 , 130.2 , 121.4 , 118.8 ( q , j = 
 319.5 hz ) , 63.6 , 31.7 , 30.1 , 21.0 . ir ( neat ) :  = 1737 , 1501 , 1419 , 
 1367 , 1246 , 1205 , 1179 , 1135 , 1039 , 1017 , 884 , 846 , 813 , 734 , 638 , 
 606 , 568 , 535 , 517 , 498 cm . hrms ( esi ) : m / z calcd for c12h13f3o5sna [ m + na ] 349.0333 , found 
 349.0334 .