Iridium-Catalyzed Reactions of ω-Arylalkanols to α,ω-Diarylalkanes

被引:57
作者
Obora, Yasushi [1 ,2 ]
Anno, Yuka [1 ,2 ]
Okamoto, Ryuhei [1 ,2 ]
Matsu-ura, Toyomi [1 ,2 ]
Ishii, Yasutaka [1 ,2 ]
机构
[1] Kansai Univ, Fac Chem Mat & Bioengn, Dept Chem & Mat Engn, Osaka 5648680, Japan
[2] Kansai Univ, ORDIST, Osaka 5648680, Japan
关键词
beta alkylation; decarbonylation; homogeneous catalysis; iridium; synthetic methods; PRIMARY ALCOHOLS; SECONDARY ALCOHOLS; BETA-ALKYLATION; TRANSFER HYDROGENATION; BORROWING HYDROGEN; GUERBET REACTION; ALDEHYDES; DECARBONYLATION; LIGAND; ALPHA;
D O I
10.1002/anie.201104452
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The long and the short of it: An atom-economical route to α,ω-diarylalkanes from ω-arylalkanols was achieved by a direct one-step method, or a sequential two-step method depending on the alkyl chain length. The reaction proceeded through the formation of β-methylhydroxy- α,ω-diarylalkanes by dehydrogenation/β-alkylation, followed by dehydrogenation/decarbonylation. Copyright © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
引用
收藏
页码:8618 / 8622
页数:5
相关论文
共 56 条
[11]   Colloidal Palladium Nanoparticles with In Situ H2: Reducing System for α,β-Unsaturated Carbonyl Compoundsαα [J].
De Castro, Kathlia A. ;
Oh, Seungchan ;
Yun, Jongchan ;
Lim, Jin Kyu ;
An, Gwangil ;
Kim, Dong Kook ;
Rhee, Hakjune .
SYNTHETIC COMMUNICATIONS, 2009, 39 (19) :3509-3520
[12]   Dehydrogenation as a Substrate-Activating Strategy in Homogeneous Transition-Metal Catalysis [J].
Dobereiner, Graham E. ;
Crabtree, Robert H. .
CHEMICAL REVIEWS, 2010, 110 (02) :681-703
[13]  
Du LS, 2002, J PHYS CHEM A, V106, P7876, DOI [10.1021/jp020457q, 10.1021/jp02O457q]
[14]   Enantioselective preparation of 1,1-diarylethanes: Aldehydes as removable steering gronps for asymmetric synthesis [J].
Fessard, Thomas C. ;
Andrews, Stephen P. ;
Motoyoshi, Hajime ;
Carreira, Erick M. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (48) :9331-9334
[15]   The mechanism for the rhodium-catalyzed decarbonylation of aldehydes: A combined experimental and theoretical study [J].
Fristrup, Peter ;
Kreis, Michael ;
Palmelund, Anders ;
Norrby, Per-Ola ;
Madsen, Robert .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (15) :5206-5215
[16]   Direct β-alkylation of secondary alcohols with primary alcohols catalyzed by a Cp*lr complex [J].
Fujita, K ;
Asai, C ;
Yamaguchi, T ;
Hanasaka, F ;
Yamaguchi, R .
ORGANIC LETTERS, 2005, 7 (18) :4017-4019
[17]   Thermodynamics and kinetics of formation of intramolecular naphthalene dimer radical cation studied by near-IR transient absorption spectroscopy [J].
Fushimi, T ;
Fujita, Y ;
Ohkita, H ;
Ito, S .
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 2004, 77 (08) :1443-1448
[18]   Alcohols as electrophiles in C-C bond-forming reactions:: The hydrogen autotransfer process [J].
Guillena, Gabriela ;
Ramon, Diego J. ;
Yus, Miguel .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (14) :2358-2364
[19]   Hydrogen Autotransfer in the N-Alkylation of Amines and Related Compounds using Alcohols and Amines as Electrophiles [J].
Guillena, Gabriela ;
Ramon, Diego J. ;
Yus, Miguel .
CHEMICAL REVIEWS, 2010, 110 (03) :1611-1641
[20]   An Olefination via Ruthenium-Catalyzed Decarbonylative Addition of Aldehydes to Terminal Alkynes [J].
Guo, Xiangyu ;
Wang, Jun ;
Li, Chao-Jun .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (42) :15092-+