Rhodium-Mediated Decarboxylative Conjugate Addition of Fluorinated Benzoic Acids: Stoichiometric and Catalytic Transformations

被引:106
作者
Sun, Zhong-Ming [1 ]
Zhao, Pinjing [1 ]
机构
[1] N Dakota State Univ, Dept Chem & Mol Biol, Fargo, ND 58105 USA
关键词
carboxylic acids; conjugate addition; decarboxylation; Heck-Mizoroki reaction; rhodium; TRANSITION-METAL ORGANOMETALLICS; C-H; BIARYL SYNTHESIS; ASYMMETRIC 1,4-ADDITION; AROMATIC CARBOXYLATES; CARBON BOND; ARYL; COMPLEXES; REARRANGEMENT; PALLADATION;
D O I
10.1002/anie.200901097
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Depending on the bisphosphine ligand, the decarboxylation of 2,6-difluorinated benzoic acids with a RhI catalyst in the presence of an acrylic ester or acrylamide led preferentially to conjugate addition (product 1) or Heck-Mizoroki arylation (product 2; binap=2,2′ -bis (diphenylphosphanyl)-1,1′ -binaphthyl, diop=4,5-bis (diphenylphosphanylmethyl)-2,2-dimethyl-1,3-dioxolane). © 2009 Wiley-VCH Verlag GmbH & Co. KCaA.
引用
收藏
页码:6726 / 6730
页数:5
相关论文
共 48 条
[1]   New η5- and μ-(O)-Rh(I) phenoxide complexes:: synthesis, characterisation and unconventional reactivity of η5-complexes towards carbon dioxide [J].
Aresta, M ;
Dibenedetto, A ;
Pascale, M ;
Quaranta, E ;
Tommasi, I .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2000, 605 (02) :143-150
[2]   Biaryl synthesis via decarboxylative Pd-catalyzed reactions of arenecarboxylic acids and diaryliodonium triflates [J].
Becht, Jean-Michel ;
Le Drian, Claude .
ORGANIC LETTERS, 2008, 10 (14) :3161-3164
[3]   Synthesis of biaryls via decarboxylative Pd-catalyzed cross-coupling reaction [J].
Becht, Jean-Michel ;
Catala, Cedric ;
Le Drian, Claude ;
Wagner, Alain .
ORGANIC LETTERS, 2007, 9 (09) :1781-1783
[4]   Two methods for direct ortho-arylation of benzoic acids [J].
Chiong, Hendrich A. ;
Pham, Quynh-Nhu ;
Daugulis, Olafs .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (32) :9879-9884
[5]   DECARBOXYLATION SYNTHESES OF TRANSITION-METAL ORGANOMETALLICS .6. PREPARATIONS OF POLYFLUOROPHENYLIRIDIUM(I) COMPOUNDS [J].
DEACON, GB ;
FAULKS, SJ .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1992, 437 (1-2) :239-249
[6]   DECARBOXYLATION SYNTHESES OF TRANSITION-METAL ORGANOMETALLICS .2. TRANS-CARBONYL(POLYHALOGENOPHENYL)BIS(TRIPHENYLPHOSPHINE)RHODIUM(I) COMPOUNDS [J].
DEACON, GB ;
FAULKS, SJ ;
MILLER, JM .
TRANSITION METAL CHEMISTRY, 1980, 5 (05) :305-313
[7]   Development of a catalytic aromatic decarboxylation reaction [J].
Dickstein, Joshua S. ;
Mulrooney, Carol A. ;
O'Brien, Erin M. ;
Morgan, Barbara J. ;
Kozlowski, Marisa C. .
ORGANIC LETTERS, 2007, 9 (13) :2441-2444
[8]   METALATION AND CARBOXYLATION OF ACTIVATED CARBON-HYDROGEN BONDS BY COMPLEXES OF IRIDIUM AND RHODIUM [J].
ENGLISH, AD ;
HERSKOVITZ, T .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1977, 99 (05) :1648-1649
[9]   Rhodium-catalyzed carbon-carbon bond forming reactions of organometallic compounds [J].
Fagnou, K ;
Lautens, M .
CHEMICAL REVIEWS, 2003, 103 (01) :169-196
[10]   Rhodium-catalyzed addition of alcohols to terminal enones [J].
Farnworth, MV ;
Cross, MJ ;
Louie, J .
TETRAHEDRON LETTERS, 2004, 45 (40) :7441-7443