Palladium-catalyzed decarboxylative sp(3)-sp(3) coupling of nitrobenzene acetic esters
Allylic esters of nitrobenzene acetic acids undergo facile palladium-catalyzed decarboxylative coupling. Both mono- and dinitroarene substrates give high yields of the coupled products. Moreover, the rates of the reactions suggest that decarboxylation is rate-limiting and substrates that sterically...
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| Published in | Journal of the American Chemical Society Vol. 129; no. 48; pp. 14860 - 14862 |
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| Main Authors | , |
| Format | Journal Article |
| Language | English |
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WASHINGTON
Amer Chemical Soc
05.12.2007
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| Abstract | Allylic esters of nitrobenzene acetic acids undergo facile palladium-catalyzed decarboxylative coupling. Both mono- and dinitroarene substrates give high yields of the coupled products. Moreover, the rates of the reactions suggest that decarboxylation is rate-limiting and substrates that sterically disfavor attainment of the reactive conformation for decarboxylation are not viable. Finally, reduction of the product nitroarenes to the corresponding anilines provides access to a variety of heterocycles including quinolines and dihydroquinolones. |
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| AbstractList | Allylic esters of nitrobenzene acetic acids undergo facile palladium-catalyzed decarboxylative coupling. Both mono- and dinitroarene substrates give high yields of the coupled products. Moreover, the rates of the reactions suggest that decarboxylation is rate-limiting and substrates that sterically disfavor attainment of the reactive conformation for decarboxylation are not viable. Finally, reduction of the product nitroarenes to the corresponding anilines provides access to a variety of heterocycles including quinolines and dihydroquinolones. |
| Author | Waetzig, Shelli R. Tunge, Jon A. |
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| Cites_doi | 10.1002/adsc.200600383 10.1021/ja070116w 10.1021/ol0514909 10.1002/anie.200461432 10.1021/ja0542688 10.1002/anie.200502018 10.1002/anie.200600721 10.1021/ja068993+ 10.1021/op0341667 10.1126/science.1128684 10.1021/ja055968f 10.1021/ol048149t 10.1021/ja074008l 10.1021/ja052099l 10.1021/jo0621569 10.1002/anie.200601889 10.1021/ja027523m |
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| Keywords | CARBOXYLATES OLEFINATION ACIDS ALLYLATION ALKYL-HALIDES |
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| References | Waetzig, SR (WOS:000245723800015) 2007; 129 Myers, AG (WOS:000178104600013) 2002; 124 Imao, D (WOS:000244390800015) 2007; 72 IOUSSAINI O (WOS:000251293500014.12) 1984; 40 Mohr, JT (WOS:000233142900026) 2005; 44 IOUSSAINI O (WOS:000251293500014.11) 1938 You, SL (WOS:000239913400002) 2006; 45 Bull, DJ (WOS:A1996UY31500020) 1996 Hadei, N (WOS:000231294400052) 2005; 7 Goossen, LJ (WOS:000245739700048) 2007; 129 Saito, B (WOS:000248484400035) 2007; 129 Goossen, LJ (WOS:000239667500041) 2006; 313 Trost, BM (WOS:000233917500026) 2005; 127 Burger, EC (WOS:000224691900059) 2004; 6 Waetzig, SR (WOS:000239543300021) 2006; 45 Dongol, KG (WOS:000246990200002) 2007; 349 Tanaka, D (WOS:000230700700049) 2005; 127 Frisch, AC (WOS:000226711700002) 2005; 44 ONO N (WOS:000251293500014.15) 2001 Rayabarapu, DK (WOS:000232257100034) 2005; 127 Hoogenraad, M (WOS:000221623200025) 2004; 8 |
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Crystallographic characterization of non-phosphine palladium(II) intermediates and observation of their stepwise transformation in Heck-like processes publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY doi: 10.1021/ja052099l contributor: fullname: Tanaka, D – volume: 72 start-page: 1652 year: 2007 ident: WOS:000244390800015 article-title: Easy access to esters with a benzylic quaternary carbon center from diallyl malonates by palladium-catalyzed decarboxylative allylation publication-title: JOURNAL OF ORGANIC CHEMISTRY doi: 10.1021/jo0621569 contributor: fullname: Imao, D – volume: 45 start-page: 5246 year: 2006 ident: WOS:000239913400002 article-title: Enantioselective palladium-catalyzed decarboxylative allylic alkylations publication-title: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION doi: 10.1002/anie.200601889 contributor: fullname: You, SL – volume: 124 start-page: 11250 year: 2002 ident: WOS:000178104600013 article-title: Development of a decarboxylative palladation reaction and its use in a Heck-type olefination of arene carboxylates publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY doi: 10.1021/ja027523m contributor: fullname: Myers, AG |
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| Snippet | Allylic esters of nitrobenzene acetic acids undergo facile palladium-catalyzed decarboxylative coupling. Both mono- and dinitroarene substrates give high... |
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| Title | Palladium-catalyzed decarboxylative sp(3)-sp(3) coupling of nitrobenzene acetic esters |
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