Palladium-Catalyzed Direct Ethynylation of C(sp3)-H Bonds in Aliphatic Carboxylic Acid Derivatives

被引:332
作者
Ano, Yusuke [1 ]
Tobisu, Mamoru [1 ,2 ]
Chatani, Naoto [1 ]
机构
[1] Osaka Univ, Fac Engn, Dept Appl Chem, Suita, Osaka 5650871, Japan
[2] Osaka Univ, Grad Sch Engn, Ctr Atom & Mol Technol, Suita, Osaka 5650871, Japan
关键词
C-H BONDS; GACL3-CATALYZED ORTHO-ETHYNYLATION; CARBON-HYDROGEN BONDS; DIRECT ALKYNYLATION; TERMINAL ALKYNES; COUPLING REACTIONS; ACTIVATION; COPPER; ARYLATION; FUNCTIONALIZATION;
D O I
10.1021/ja206002m
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The first catalytic alkynylation of unactivated C(sp(3))-H bonds has been accomplished. The method allows for the straightforward introduction of an ethynyl group into aliphatic acid derivatives under palladium catalysis. This new reaction can be applied to the rapid elaboration of complex aliphatic acids, for example, via azide/alkyne cycloaddition.
引用
收藏
页码:12984 / 12986
页数:3
相关论文
共 62 条
[41]   Transition-Metal-Catalyzed Direct C-H Alkenylation, Alkynylation, Benzylation, and Alkylation of (Hetero)arenes [J].
Messaoudi, Samir ;
Brion, Jean-Daniel ;
Alami, Mouad .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2010, 2010 (34) :6495-6516
[42]  
MURATA S, 1993, J CHEM RES-S, P434
[43]   Novel acetoxylation and C-C coupling reactions at unactivated positions in α-amino acid derivatives [J].
Reddy, B. V. Subba ;
Reddy, Leleti Rajender ;
Corey, E. J. .
ORGANIC LETTERS, 2006, 8 (15) :3391-3394
[44]   Palladium-catalysed direct alkenylation of sydnones [J].
Rodriguez, Arantxa ;
Fennessy, Rebecca V. ;
Moran, Wesley J. .
TETRAHEDRON LETTERS, 2009, 50 (27) :3942-3944
[45]   Direct palladium-catalyzed alkynylation of N-fused heterocycles [J].
Seregin, Ilya V. ;
Ryabova, Victoria ;
Gevorgyan, Vladimir .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (25) :7742-+
[46]   Catalytic coupling of C-H and C-I bonds using pyridine as a directing group [J].
Shabashov, D ;
Daugulis, O .
ORGANIC LETTERS, 2005, 7 (17) :3657-3659
[47]   Auxiliary-Assisted Palladium-Catalyzed Arylation and Alkylation of sp2 and sp3 Carbon-Hydrogen Bonds [J].
Shabashov, Dmitry ;
Daugulis, Olafs .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (11) :3965-3972
[48]   PdII-catalyzed enantioselective activation of C(sp2)-H and C(sp3)-H bonds using monoprotected amino acids as chiral ligands [J].
Shi, Bing-Feng ;
Maugel, Nathan ;
Zhang, Yang-Hui ;
Yu, Jin-Quan .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (26) :4882-4886
[49]   Aerobic Pd-Catalyzed sp3 C-H Olefination: A Route to Both N-Heterocyclic Scaffolds and Alkenes [J].
Stowers, Kara J. ;
Fortner, Kevin C. ;
Sanford, Melanie S. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (17) :6541-6544
[50]   Direct C-H Transformation via Iron Catalysis [J].
Sun, Chang-Liang ;
Li, Bi-Jie ;
Shi, Zhang-Jie .
CHEMICAL REVIEWS, 2011, 111 (03) :1293-1314