Transition metal-free C(sp3)-H bond coupling among three methyl groups

被引：60

作者：

Liu, Yufeng ^{[1
]}

Zhan, Xi ^{[1
]}

Ji, Pengyi ^{[1
]}

Xu, Jingwen ^{[1
]}

Liu, Qiang ^{[1
]}

Luo, Weiping ^{[1
]}

Chen, Tieqiao ^{[1
]}

Guo, Cancheng ^{[1
]}

机构：

[1] Hunan Univ, Coll Chem & Chem Engn, Changsha 410082, Hunan, Peoples R China

来源：

CHEMICAL COMMUNICATIONS | 2017年 / 53卷 / 38期

基金：

中国国家自然科学基金;

关键词：

C-H BONDS; BAYLIS-HILLMAN REACTION; CARBON-HYDROGEN BONDS; OXIDATIVE ACTIVATION; CATALYZED ARYLATION; AMINO-ACIDS; FUNCTIONALIZATION; ALKYLATION; SP(2); STRATEGY;

D O I：

10.1039/c7cc01309d

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A coupling of multiple C(sp(3))-H bonds of the methyl group in methyl ketones with dimethyl sulfoxide is developed. This coupling allows the direct C(sp(3))-H bond coupling among three methyl groups and affords one C-C bond and one CQC bond under transition metal-free conditions. The value-added cyclized 3-methylthiomethyl chroman-4-ones can be synthesized through this method. A plausible mechanism is proposed.

引用

页码：5346 / 5349

页数：4

共 36 条

[1] [Anonymous], 2004, METAL CATALYZED CROS
[2] Transition metal-catalyzed arylation of unactivated C(sp3)-H bonds
Baudoin, Olivier
[J]. CHEMICAL SOCIETY REVIEWS, 2011, 40 (10) : 4902 - 4911
[3] Beller M., 2004, Transition Metals for Organic Synthesis, V1
[4] Transition Metal-Catalyzed Direct Arylation of Substrates with Activated sp3-Hybridized C-H Bonds and Some of Their Synthetic Equivalents with Aryl Halides and Pseudohalides
Bellina, Fabio
Rossi, Renzo
[J]. CHEMICAL REVIEWS, 2010, 110 (02) : 1082 - 1146
[5] Catalytic asymmetric cross-dehydrogenative coupling: activation of C-H bonds by a cooperative bimetallic catalyst system
Cao, Weidi
Liu, Xiaohua
Peng, Ruixue
He, Peng
Lin, Lili
Feng, Xiaoming
[J]. CHEMICAL COMMUNICATIONS, 2013, 49 (33) : 3470 - 3472
[6] Sulfonamide-Promoted Palladium(II)-Catalyzed Alkylation of Unactivated Methylene C(sp3)-H Bonds with Alkyl Iodides
Chen, Kai
Shi, Bing-Feng
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (44) : 11950 - 11954
[7] Palladium-catalyzed alkylation of sp2 and sp3 C-H bonds with methylboroxine and alkylboronic acids:: Two distinct C-H activation pathways
Chen, Xiao
Goodhue, Charles E.
Yu, Jin-Quan
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (39) : 12634 - 12635
[8] Synthesis and Evaluation of Substituted Chroman-4-one and Chromone Derivatives as Sirtuin 2-Selective Inhibitors
Friden-Saxin, Maria
Seifert, Tina
Landergren, Marie Ryden
Suuronen, Tiina
Lahtela-Kakkonen, Maija
Jarho, Elina M.
Luthman, Kristina
[J]. JOURNAL OF MEDICINAL CHEMISTRY, 2012, 55 (16) : 7104 - 7113
[9] The Cross-Dehydrogenative Coupling of Csp3-H Bonds: A Versatile Strategy for C-C Bond Formations
Girard, Simon A.
Knauber, Thomas
Li, Chao-Jun
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (01) : 74 - 100
[10] C-H functionalization logic in total synthesis
Gutekunst, Will R.
Baran, Phil S.
[J]. CHEMICAL SOCIETY REVIEWS, 2011, 40 (04) : 1976 - 1991

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