Palladium-catalyzed nucleomethylation of alkynes for synthesis of methylated heteroaromatic compounds

被引：13

作者：

Yang, Xi ^{[1
]}

Wang, Gang ^{[1
]}

Ye, Zhi-Shi ^{[1
]}

机构：

[1] Dalian Univ Technol, Zhang Dayu Sch Chem, Dalian 116024, Peoples R China

来源：

CHEMICAL SCIENCE | 2022年 / 13卷 / 34期

基金：

中国国家自然科学基金;

关键词：

C-H FUNCTIONALIZATION; ARYLBORONIC ACIDS; RECENT PROGRESS; ARYL HALIDES; INDOLES; ALKYLATION; REAGENTS; BOND; GRIGNARD; METHYLALUMINUM;

D O I：

10.1039/d2sc03294e

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Herein, we disclosed a novel and efficient palladium-catalyzed nucleomethylation of alkynes for the simultaneous construction of the heteroaromatic ring and methyl group. The 3-methylindoles, 3-methylbenzofurans and 4-methylisoquinolines were obtained in moderate to excellent yields. Notably, this methodology was employed as a key step for synthesis of a pregnane X receptor antagonist, zindoxifene, bazedoxifene and AFN-1252. The kinetic studies revealed that reductive elimination might be the rate-determining step.

引用

页码：10095 / 10102

页数：8

共 103 条

[91] Structure-based optimization of protein tyrosine phosphatase 1B inhibitors: From the active site to the second phosphotyrosine binding site [J].

Wilson, Douglas P. ;

Wan, Zhao-Kui ;

Xu, Wei-Xin ;

Kirincich, Steven J. ;

Follows, Bruce C. ;

Joseph-McCarthy, Diane ;

Foreman, Kenneth ;

Moretto, Alessandro ;

Wu, Junjun ;

Zhu, Min ;

Binnun, Eva ;

Zhang, Yan-Ling ;

Tam, May ;

Erbe, David V. ;

Tobin, James ;

Xu, Xin ;

Leung, Louis ;

Shilling, Adam ;

Tam, Steve Y. ;

Mansour, Tarek S. ;

Lee, Jinbo .

JOURNAL OF MEDICINAL CHEMISTRY, 2007, 50 (19) :4681-4698

[92] Pd-Catalyzed Alkylation of (Iso)quinolines and Arenes: 2-Acylpyridine Compounds as Alkylation Reagents [J].

Wu, Qingsong ;

Han, Shuaijun ;

Ren, Xiaoxiao ;

Lu, Hongtao ;

Li, Jingya ;

Zou, Dapeng ;

Wu, Yangjie ;

Wu, Yusheng .

ORGANIC LETTERS, 2018, 20 (20) :6345-6348

[93]

Wu Y.-J., 2010, HETEROCYCLIC SCAFFOL

[94] Pd-Catalyzed ipso,meta-Dimethylation of ortho-Substituted Iodoarenes via a Base-Controlled C-H Activation Cascade with Dimethyl Carbonate as the Methyl Source [J].

Wu, Zhuo ;

Wei, Feng ;

Wan, Bin ;

Zhang, Yanghui .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2021, 143 (12) :4524-4530

[95] Alkali-amide controlled selective synthesis of 7-azaindole and 7-azaindoline through domino reactions of 2-fluoro-3-methylpyridine and aldehydes [J].

Xu, Xinyu ;

Ou, Mingjie ;

Wang, Yan-En ;

Lin, Tingzhi ;

Xiong, Dan ;

Xue, Fei ;

Walsh, Patrick J. ;

Mao, Jianyou .

ORGANIC CHEMISTRY FRONTIERS, 2022, 9 (09) :2541-2548

[96] SYNTHESIS OF MULTISUBSTITUTED BENZOFURANS/INDOLES USING MULTICHLORINATED PHENOLS/ANILINES VIA PALLADIUM-CATALYZED SITE-SELECTIVE SONOGASHIRA COUPLING [J].

Yamaguchi, Miyuki ;

Manabe, Kei .

HETEROCYCLES, 2022, 104 (01) :3-26

[97] One-Pot Synthesis of 2,4-Disubstituted Indoles from N-Tosyl-2,3-dichloroaniline Using Palladium-Dihydroxyterphenylphosphine Catalyst [J].

Yamaguchi, Miyuki ;

Manabe, Kei .

ORGANIC LETTERS, 2014, 16 (09) :2386-2389

[98] Alkyne activation with Bronsted acids, iodine, or gold complexes, and its fate leading to synthetic application [J].

Yamamoto, Yoshinori ;

Gridnev, Ilya D. ;

Patil, Nitin T. ;

Jin, Tienan .

CHEMICAL COMMUNICATIONS, 2009, (34) :5075-5087

[99] Recent Advances in Transition Metal-Catalyzed Methylation Reactions [J].

Yan, Guobing ;

Borah, Arun Jyoti ;

Wang, Lianggui ;

Yang, Minghua .

ADVANCED SYNTHESIS & CATALYSIS, 2015, 357 (07) :1333-1350

[100] Transition-Metal-Catalyzed Enantioselective Synthesis of Indoles from 2-Alkynylanilines [J].

Ye, Zhi-Shi ;

Li, Jin-Chen ;

Wang, Gang .

SYNTHESIS-STUTTGART, 2022, 54 (09) :2133-2147

← 2 3 4 5 6 7 8 9 10 11 →