Rhodium-Catalyzed Ketone Methylation Using Methanol Under Mild Conditions: Formation of α-Branched Products

被引：217

作者：

Chan, Louis K. M. ^{[1
]}

Poole, Darren L. ^{[1
]}

Shen, Di ^{[1
]}

Healy, Mark P. ^{[1
]}

Donohoe, Timothy J. ^{[1
]}

机构：

[1] Univ Oxford, Dept Chem, Chem Res Lab, Oxford OX1 3TA, England

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2014年 / 53卷 / 03期

基金：

英国工程与自然科学研究理事会;

关键词：

homogeneous catalysis; hydrogen borrowing; ketones; methanol; TRANSITION-METAL-COMPLEXES; C BOND FORMATION; BORROWING HYDROGEN; PRIMARY ALCOHOLS; CARBONYL ADDITION; ALKYLATION; OXIDATION; ACTIVATION; ARYLACETONITRILES; MONOALKYLATION;

D O I：

10.1002/anie.201307950

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The rhodium-catalyzed methylation of ketones has been accomplished using methanol as the methylating agent and the hydrogen-borrowing method. The sequence is notable for the relatively low temperatures that are required and for the ability of the reaction system to form alpha-branched products with ease. Doubly alkylated ketones can be prepared from methyl ketones and two different alcohols by using a sequential one-pot iridium- and rhodium-catalyzed process.

引用

页码：761 / 765

页数：5

共 53 条

[21] Borrowing hydrogen in the activation of alcohols [J].

Hamid, Malai Haniti S. A. ;

Slatford, Paul A. ;

Williams, Jonathan M. J. .

ADVANCED SYNTHESIS & CATALYSIS, 2007, 349 (10) :1555-1575

[22] Iridium-Catalyzed α-Alkylation of Acetates with Primary Alcohols and Diols [J].

Iuchi, Yosuke ;

Obora, Yasushi ;

Ishii, Yasutaka .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (08) :2536-+

[23] ON A RHODIUM COMPLEX WITH CARBON DIOXIDE [J].

IWASHITA, Y ;

HAYATA, A .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1969, 91 (10) :2525-&

[24] Mechanistic Investigations of the Iridium(III)-Catalyzed Aerobic Oxidation of Primary and Secondary Alcohols [J].

Jiang, Bi ;

Feng, Yuee ;

Ison, Elon A. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (44) :14462-+

[25] RuHCl(CO)(PPh3)3-Catalyzed α-Alkylation of Ketones with Primary Alcohols [J].

Kuwahara, Takashi ;

Fukuyama, Takahide ;

Ryu, Ilhyong .

ORGANIC LETTERS, 2012, 14 (18) :4703-4705

[26]

Kwon MinSerk., 2005, ANGEW CHEMIE, V117, P7073, DOI [10.1002/ange.200502422., DOI 10.1002/ANGE.200502422]

[27] Recyclable palladium catalyst for highly selective α alkylation of ketones with alcohols [J].

Kwon, MS ;

Khn, N ;

Seo, SH ;

Park, IS ;

Cheedrala, RK ;

Park, J .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (42) :6913-6915

[28] Stepwise MetalLigand Cooperation by a Reversible Aromatization/Deconjugation Sequence in Ruthenium Complexes with a Tetradentate Phenanthroline-Based Ligand [J].

Langer, Robert ;

Fuchs, Ido ;

Vogt, Matthias ;

Balaraman, Ekambaram ;

Diskin-Posner, Yael ;

Shimon, Linda J. W. ;

Ben-David, Yehoshoa ;

Milstein, David .

CHEMISTRY-A EUROPEAN JOURNAL, 2013, 19 (10) :3407-3414

[29] General and efficient method for direct N-monomethylation of aromatic primary amines with methanol [J].

Li, Feng ;

Xie, Jianjiang ;

Shan, Haixia ;

Sun, Chunlou ;

Chen, Lin .

RSC ADVANCES, 2012, 2 (23) :8645-8652

[30] Chemoselective Conjugate Reduction of α,β-Unsaturated Ketones Catalyzed by Rhodium Amido Complexes in Aqueous Media [J].

Li, Xuefeng ;

Li, Liangchun ;

Tang, Yuanfu ;

Zhong, Ling ;

Cun, Linfeng ;

Zhu, Jin ;

Liao, Jian ;

Deng, Jingen .

JOURNAL OF ORGANIC CHEMISTRY, 2010, 75 (09) :2981-2988

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