Recent Advances in Transition Metal-Catalyzed Methylation Reactions

被引:133
作者
Yan, Guobing [1 ]
Borah, Arun Jyoti [1 ]
Wang, Lianggui [1 ]
Yang, Minghua [1 ]
机构
[1] Lishui Univ, Dept Chem, Lishui City 323000, Peoples R China
关键词
cross-coupling; methylation; transition metal catalysts; C-H BONDS; CARBON-DIOXIDE; N-METHYLATION; COUPLING REACTIONS; VINYL HALIDES; ALPHA-METHYLATION; C(SP(3))-H BONDS; CARBOXYLIC-ACIDS; AROMATIC-AMINES; NITRO-COMPOUNDS;
D O I
10.1002/adsc.201400984
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
Methylation is one of the most fundamental synthetic transformations in organic chemistry, but usually employs hazardous and toxic reagents, such as methyl iodide, dimethyl sulfate, diazomethane and dimethyl carbonate. In order to address sustainable development and green strategies, synthetic chemists have devoted much effort to the discovery and development of new methylating reagents, which are successfully being applied in transition metal-catalyzed cross-coupling reactions. In this review, recent advances in this area are summarized, mainly including C-methylation, N-methylation and O-methylation. The respective reaction mechanisms are also discussed.
引用
收藏
页码:1333 / 1350
页数:18
相关论文
共 129 条
[31]   Palladium-catalyzed alkylation of aryl C-H bonds with sp3 organotin reagents using benzoquinone as a crucial promoter [J].
Chen, X ;
Li, JJ ;
Hao, XS ;
Goodhue, CE ;
Yu, JQ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (01) :78-79
[32]   Palladium-catalyzed alkylation of sp2 and sp3 C-H bonds with methylboroxine and alkylboronic acids:: Two distinct C-H activation pathways [J].
Chen, Xiao ;
Goodhue, Charles E. ;
Yu, Jin-Quan .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (39) :12634-12635
[33]   S-adenosylmethionine and methylation [J].
Chiang, PK ;
Gordon, RK ;
Tal, J ;
Zeng, GC ;
Doctor, BP ;
Pardhasaradhi, K ;
McCann, PP .
FASEB JOURNAL, 1996, 10 (04) :471-480
[34]   The sonogashira reaction:: A booming methodology in synthetic organic chemistry [J].
Chinchilla, Rafael ;
Najera, Carmen .
CHEMICAL REVIEWS, 2007, 107 (03) :874-922
[35]   User-friendly methylation of aryl and vinyl halides and pseudohalides with DABAL-Me3 [J].
Cooper, T ;
Novak, A ;
Humphreys, LD ;
Walker, MD ;
Woodward, S .
ADVANCED SYNTHESIS & CATALYSIS, 2006, 348 (06) :686-690
[36]   N-Methylation of amine and nitro compounds with CO2/H2 catalyzed by Pd/CuZrOx under mild reaction conditions [J].
Cui, Xinjiang ;
Zhang, Yan ;
Deng, Youquan ;
Shi, Feng .
CHEMICAL COMMUNICATIONS, 2014, 50 (88) :13521-13524
[37]   Methylation of amines, nitrobenzenes and aromatic nitriles with carbon dioxide and molecular hydrogen [J].
Cui, Xinjiang ;
Dai, Xingchao ;
Zhang, Yan ;
Deng, Youquan ;
Shi, Feng .
CHEMICAL SCIENCE, 2014, 5 (02) :649-655
[38]   Divergent C-H Functionalizations Directed by Sulfonamide Pharmacophores: Late-Stage Diversification as a Tool for Drug Discovery [J].
Dai, Hui-Xiong ;
Stepan, Antonia F. ;
Plummer, Mark S. ;
Zhang, Yang-Hui ;
Yu, Jin-Quan .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (18) :7222-7228
[39]   Di-tert Butyl Peroxide-Promoted Sequential Methylation and Intramolecular Aromatization of Isonitriles [J].
Dai, Qiang ;
Yu, Jin-Tao ;
Feng, Xiaomei ;
Jiang, Yan ;
Yang, Haitao ;
Cheng, Jiang .
ADVANCED SYNTHESIS & CATALYSIS, 2014, 356 (16) :3341-3346
[40]   The carbomethylation of arylacrylamides leading to 3-ethyl-3-substituted indolin-2-one by cascade radical addition/cyclization [J].
Dai, Qiang ;
Yu, Jintao ;
Jiang, Yan ;
Guo, Songjin ;
Yang, Haitao ;
Cheng, Jiang .
CHEMICAL COMMUNICATIONS, 2014, 50 (29) :3865-3867