Benzylarylation of N-AllyI Anilines: Synthesis of Benzylated Indolines

被引：25

作者：

Huang, Wenzhong ^{[1
]}

Li, Xiulan ^{[1
]}

Song, Xuemei ^{[1
]}

Luo, Qing ^{[1
]}

Li, Yanping ^{[1
]}

Dong, Ying ^{[2
]}

Liang, Deqiang ^{[1
,3
]}

Wang, Baoling ^{[1
,3
]}

机构：

[1] Kunming Univ, Dept Chem, Kunming 650214, Yunnan, Peoples R China

[2] Shandong Normal Univ, Coll Chem Chem Engn & Mat Sci, Jinan 250014, Shandong, Peoples R China

[3] Yunnan Engn Technol Res Ctr Plast Films, Kunming 650214, Yunnan, Peoples R China

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2019年 / 84卷 / 10期

基金：

中国国家自然科学基金;

关键词：

C-H BONDS; HIGHLY EFFICIENT ACCESS; FREE DIRECT ALKYLATION; C(SP(3))-H BONDS; OXIDATIVE CYCLIZATION; TOLUENE DERIVATIVES; ACTIVATED ALKYNES; FUNCTIONALIZATION; CATALYSIS; SP(3);

D O I：

10.1021/acs.joc.9b00237

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An unprecedented benzylic C-H functionalization of methyl arenes across unactivated alkenes is presented. In the presence of MnCl2 center dot 4H(2)O and di-tert-butyl peroxide, N-allyl anilines underwent benzylation/cyclization cascade to give benzylated indolines, which are a previously unmet synthetic goal. This protocol features simple operation, broad substrate scope, and great exo selectivity.

引用

页码：6072 / 6083

页数：12

共 50 条

[21] Synthesis and antimalarial activity of N-benzylated (N-arylcarbamoyl) alkylphosphonic acid derivatives
Adeyemi, Christiana M.
Faridoon
Isaacs, Michelle
Mnkandhla, Dumisani
Hoppe, Heinrich C.
Krause, Rui W. M.
Kaye, Perry T.
BIOORGANIC & MEDICINAL CHEMISTRY, 2016, 24 (23) : 6131 - 6138
[22] SYNTHESIS OF N-(DIPHEYLMETHYL)ANILINES AND P-(DIPHENYLMETHYL)ANILINES - ESR STUDY OF THEIR PHOTOFRAGMENTATION
SISKOS, MG
GARAS, SK
ZARKADIS, AK
BOKARIS, EP
CHEMISCHE BERICHTE-RECUEIL, 1992, 125 (11): : 2477 - 2481
[23] Selective Iron Catalyzed Synthesis of N-Alkylated Indolines and Indoles
Wu, Jiajun
Tongdee, Satawat
Cordier, Marie
Darcel, Christophe
CHEMISTRY-A EUROPEAN JOURNAL, 2022, 28 (54)
[24] Synthesis and Tunability of Highly Electron-Accepting, N-Benzylated "Phosphaviologens"
Stolar, Monika
Borau-Garcia, Javier
Toonen, Mark
Baumgartner, Thomas
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2015, 137 (09) : 3366 - 3371
[25] Synthesis of N- and C-trimethylsilyl-substituded anilines
Storozhenko, P. A.
Belyakova, Z. V.
Starikova, O. A.
Nosova, V. M.
Shulyat'eva, T. I.
Frenkel, A. S.
Pecherskii, M. V.
RUSSIAN JOURNAL OF GENERAL CHEMISTRY, 2008, 78 (05) : 892 - 897
[26] SYNTHESIS OF IMIDAZOLES BY REACTION OF N-BENZYLATED AMIDINES WITH CARBOXYLIC-ACID DERIVATIVES
LIEBSCHER, J
FEIST, K
JOURNAL FUR PRAKTISCHE CHEMIE, 1988, 330 (02): : 175 - 181
[27] Synthesis of N-benzylated cobalt phthalocyaninetetrasulfonamide and its application in oxidative desulfurization catalysis
Tripathi, Deependra
Negi, Himani
Singh, Raj K.
Singh, Udai P.
Srivastava, Vimal C.
JOURNAL OF COORDINATION CHEMISTRY, 2019, 72 (17) : 2982 - 2996
[28] Synthesis of N-Alkylated Indolines and Indoles from Indoline and Aliphatic Ketones
Bayindir, Sinan
Erdogan, Esra
Kilic, Haydar
Aydin, Omer
Saracoglu, Nurullah
JOURNAL OF HETEROCYCLIC CHEMISTRY, 2015, 52 (05) : 1589 - 1594
[29] Recent Advances in the Synthesis of Indolines via Dearomative Annulation of N-acylindoles
Lu, Cong-Cong
Hao, Bo-Ya
Han, Ya-Ping
Liang, Yong-Min
ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2022, 11 (10)
[30] N-BENZYLATED POLY(VINYLAMINE) - SYNTHESIS, CHARACTERIZATION, AND CATALYTIC ACTIVITY IN ESTER CLEAVAGE
MARTEL, B
POLLET, A
MORCELLET, M
MACROMOLECULES, 1994, 27 (19) : 5258 - 5262

← 1 2 3 4 5 →