Recent Advances in Methylation: A Guide for Selecting Methylation Reagents

被引：188
作者：
Chen, Yantao [1 ]
机构：
[1] AstraZeneca Gothenburg, IMED Biotech Unit, Med Chem Cardiovasc Renal & Metab, Gothenburg, Sweden
来源：
CHEMISTRY-A EUROPEAN JOURNAL | 2019年 / 25卷 / 14期
关键词：
dimethylation; medicinal chemistry; methylation; mono N-methylation; N-methyl amino acids; N-methyl peptides; MONO-N-METHYLATION; C-H ALKYLATION; ALPHA-AMINO-ACIDS; NICKEL-CATALYZED METHYLATION; LATE-STAGE FUNCTIONALIZATION; 5-HT2C RECEPTOR AGONISTS; CROSS-COUPLING REACTIONS; SOLID-PHASE SYNTHESIS; DIMETHYL CARBONATE; REDUCTIVE METHYLATION;
D O I：
10.1002/chem.201803642
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Methylation is a well-known structural modification in organic and medicinal chemistry. This review summarizes recent advances in methylation by categorizing specific methylation reagents. The challenges of mono N-methylation of aliphatic amines and N-methylation of peptides are discussed. This review will be useful for chemists wanting to select the appropriate reagents for methylation chemistry. Based on the large diversity of methylation reagents and their wide scope, this review also broadens perspectives on which strategies to select for utilizing a particular methylation, resulting in an increased flexibility in synthetic route planning.
引用
收藏
页码：3405 / 3439
页数：35
相关论文
共 324 条
  • [1] Cobalt-catalyzed trimethylsilylmethylmagnesium-promoted radical alkenylation of alkyl halides: A complement to the heck reaction
    Affo, Walter
    Ohmiya, Hirohisa
    Fujioka, Takuma
    Ikeda, Yousuke
    Nakamura, Tomoaki
    Yorimitsu, Hideki
    Oshima, Koichiro
    Imamura, Yuki
    Mizuta, Tsutomu
    Miyoshi, Katsuhiko
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (24) : 8068 - 8077
  • [2] Iron-Catalyzed Coupling of Aryl Sulfannates and Aryl/Vinyl Tosylates with Aryl Grignards
    Agrawal, Toolika
    Cook, Silas P.
    [J]. ORGANIC LETTERS, 2014, 16 (19) : 5080 - 5083
  • [3] Tricyclic dihydroquinazolinones as novel 5-HT2C selective and orally efficacious anti-obesity agents
    Ahmad, Saleem
    Ngu, Khehyong
    Miller, Keith J.
    Wu, Ginger
    Hung, Chen-pin
    Malmstrom, Sarah
    Zhang, Ge
    O'Tanyi, Eva
    Keim, William J.
    Cullen, Mary Jane
    Rohrbach, Kenneth W.
    Thomas, Michael
    Ung, Thao
    Qu, Qinling
    Gan, Jinping
    Narayanan, Rangaraj
    Pelleymounter, Mary Ann
    Robl, Jeffrey A.
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2010, 20 (03) : 1128 - 1133
  • [4] The Nickel(II)-Catalyzed Direct Benzylation, Allylation, Alkylation, and Methylation of C-H Bonds in Aromatic Amides Containing an 8-Aminoquinoline Moiety as the Directing Group
    Aihara, Yoshinori
    Wuelbern, Jendrik
    Chatani, Naoto
    [J]. BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 2015, 88 (03) : 438 - 446
  • [5] Safe and Efficient Reductive Methylation of Primary and Secondary Amines Using N-Methylpyrrolidine Zinc Borohydride
    Alinezhad, Heshmatollah
    Tajbakhsh, Mahmood
    Salehian, Fatemeh
    Fazli, Kazem
    [J]. SYNTHETIC COMMUNICATIONS, 2010, 40 (16) : 2415 - 2420
  • [6] [Anonymous], 2016, ANGEW CHEM INT EDIT
  • [7] Dimethylcarbonate: a modern green reagent and solvent
    Arico, F.
    Tundo, P.
    [J]. RUSSIAN CHEMICAL REVIEWS, 2010, 79 (06) : 479 - 489
  • [8] Pd0-Catalyzed carbonylation of 1,1-dichloro-1-alkenes, a new selective access to Z-α-chloroacrylates
    Arthuis, Martin
    Lecup, Anne
    Roulland, Emmanuel
    [J]. CHEMICAL COMMUNICATIONS, 2010, 46 (41) : 7810 - 7812
  • [9] Dimethylsulfoxide as an N-Methylation Reagent for Amines and Aromatic Nitro Compounds
    Atkinson, Benjamin N.
    Williams, Jonathan M. J.
    [J]. CHEMCATCHEM, 2014, 6 (07) : 1860 - 1862
  • [10] N-METHYLATION OF AMIDES, LACTAMS, AND UREAS
    AUERBACH, J
    ZAMORE, M
    WEINREB, SM
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1976, 41 (04) : 725 - 726
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