Rhodium-Catalyzed Selective Olefination of Arene Esters via C-H Bond Activation

被引:264
作者
Park, Sae Hume
Kim, Ji Young
Chang, Sukbok [1 ]
机构
[1] Korea Adv Inst Sci & Technol, Dept Chem, Taejon 305701, South Korea
关键词
BENZOIC-ACIDS; AROMATIC KETONES; INTERNAL ALKYNES; CARBOXYLIC-ACIDS; DIRECT AMINATION; DIRECT ARYLATION; ARYL KETONES; DERIVATIVES; ALKENES; FUNCTIONALIZATION;
D O I
10.1021/ol200600p
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A new catalytic procedure of ortho-olefination of benzoates and benzaldehydes has been developed. Ester and carboxaldehyde units were revealed to be effective chelating groups in focusing the activation of aryl C-H bonds ortho to the directing moieties under the Rh-catalyzed oxidative conditions. The reaction is highly regioselective with a range of benzoates and benzaldehydes enabling the efficient olefination with acrylates, acrylic acid, and styrenes.
引用
收藏
页码:2372 / 2375
页数:4
相关论文
共 62 条
[1]   Transition-Metal-Catalyzed Direct Arylation of (Hetero)Arenes by C-H Bond Cleavage [J].
Ackermann, Lutz ;
Vicente, Ruben ;
Kapdi, Anant R. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (52) :9792-9826
[2]   Mechanistic Study of Acetate-Assisted C-H Activation of 2-Substituted Pyridines with [MCl2CP*]2 (M = Rh, Ir) and [RuCl2(p-cymene)]2 [J].
Boutadla, Youcef ;
Al-Duaij, Omar ;
Davies, David L. ;
Griffith, Gerald A. ;
Singh, Kuldip .
ORGANOMETALLICS, 2009, 28 (02) :433-440
[3]   Mechanistic studies of the copper-catalyzed electrophilic amination of diorganozinc reagents and development of a zinc-free protocol [J].
Campbell, Matthew J. ;
Johnson, Jeffrey S. .
ORGANIC LETTERS, 2007, 9 (08) :1521-1524
[4]   Ester to Amide Switch Peptides Provide a Simple Method for Preparing Monomeric Islet Amyloid Polypeptide under Physiologically Relevant Conditions and Facilitate Investigations of Amyloid Formation [J].
Cao, Ping ;
Raleigh, Daniel P. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (12) :4052-+
[5]   Palladium(II)-Catalyzed C-H Activation/C-C Cross-Coupling Reactions: Versatility and Practicality [J].
Chen, Xiao ;
Engle, Keary M. ;
Wang, Dong-Hui ;
Yu, Jin-Quan .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (28) :5094-5115
[6]   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
[7]   Palladium-catalyzed C-H functionalization of pyridine N-oxides:: Highly selective alkenylation and direct arylation with unactivated arenes [J].
Cho, Seung Hwan ;
Hwang, Seung Jun ;
Chang, Sukbok .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (29) :9254-+
[8]   Silver-Mediated Direct Amination of Benzoxazoles: Tuning the Amino Group Source from Formamides to Parent Amines [J].
Cho, Seung Hwan ;
Kim, Ji Young ;
Lee, S. Yunmi ;
Chang, Sukbok .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (48) :9127-9130
[9]   Rhodium-Catalyzed C-C Bond Formation via Heteroatom-Directed C-H Bond Activation [J].
Colby, Denise A. ;
Bergman, Robert G. ;
Ellman, Jonathan A. .
CHEMICAL REVIEWS, 2010, 110 (02) :624-655
[10]   Synthesis of Phenanthrone Derivatives from sec-Alkyl Aryl Ketones and Aryl Halides via a Palladium-Catalyzed Dual C-H Bond Activation and Enolate Cyclization [J].
Gandeepan, Parthasarathy ;
Parthasarathy, Kanniyappan ;
Cheng, Chien-Hong .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (25) :8569-+