Synthesis of Isochromene and Related Derivatives by Rhodium-Catalyzed Oxidative Coupling of Benzyl and Allyl Alcohols with Alkynes

被引:83
作者
Morimoto, Keisuke [1 ]
Hirano, Koji [1 ]
Satoh, Tetsuya [1 ]
Miura, Masahiro [1 ]
机构
[1] Osaka Univ, Dept Appl Chem, Fac Engn, Suita, Osaka 5650871, Japan
关键词
C-H BOND; CARBON-HYDROGEN BONDS; INTERNAL ALKYNES; ACTIVATION; FUNCTIONALIZATION; CLEAVAGE; HETEROCYCLES; ARYLATION; ALKENES; ROUTE;
D O I
10.1021/jo201923d
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The straightforward synthesis of isochromene derivatives and related cyclic ethers is achieved by the rhodium-catalyzed oxidative coupling of alpha,alpha-disubstituted benzyl and allyl alcohols with alkynes. The hydroxy groups effectively act as the key function for the regioselective C-H bond cleavage.
引用
收藏
页码:9548 / 9551
页数:4
相关论文
共 39 条
[1]   Carboxylate-Assisted Transition-Metal-Catalyzed C-H Bond Functionalizations: Mechanism and Scope [J].
Ackermann, Lutz .
CHEMICAL REVIEWS, 2011, 111 (03) :1315-1345
[2]   Novel heteroarotinoids as potential antagonists of Mycobacterium bovis BCG [J].
Brown, CW ;
Liu, SQ ;
Klucik, J ;
Berlin, KD ;
Brennan, PJ ;
Kaur, D ;
Benbrook, DM .
JOURNAL OF MEDICINAL CHEMISTRY, 2004, 47 (04) :1008-1017
[3]   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
[4]   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
[5]   Palladium- and Copper-Catalyzed Arylation of Carbon-Hydrogen Bonds [J].
Daugulis, Olafs ;
Do, Hien-Quang ;
Shabashov, Dmitry .
ACCOUNTS OF CHEMICAL RESEARCH, 2009, 42 (08) :1074-1086
[6]   C-H bond functionalization in complex organic synthesis [J].
Godula, K ;
Sames, D .
SCIENCE, 2006, 312 (5770) :67-72
[7]   A chemoselective route to either 4-methyl-2,4-dipheny1-2-pentene or 1,1,3-trimethyl-3-phenylindane from 2-phenylpropan-2-ol mediated by BiBr3: a mechanistic study [J].
Howard, Fredrick ;
Sawadjoon, Supaporn ;
Samec, Joseph S. M. .
TETRAHEDRON LETTERS, 2010, 51 (32) :4208-4210
[8]   An improved catalyst architecture for rhodium(III) catalyzed C-H activation and its application to pyridone synthesis [J].
Hyster, Todd K. ;
Rovis, Tomislav .
CHEMICAL SCIENCE, 2011, 2 (08) :1606-1610
[9]   Transition-Metal-Catalyzed Carbon-Carbon Bond Formation via Carbon-Hydrogen Bond Cleavage [J].
Kakiuchi, Fumitoshi ;
Kochi, Takuya .
SYNTHESIS-STUTTGART, 2008, (19) :3013-3039
[10]   Synthesis of Oxacycles Employing the Oxa-Pictet-Spengler Reaction: Recent Developments and New Prospects [J].
Larghi, Enrique L. ;
Kaufman, Teodoro S. .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2011, 2011 (27) :5195-5231