A Unified Strategy for Iron-Catalyzed ortho-Alkylation of Carboxamides

被引：130

作者：

Fruchey, Erin R. ^{[1
]}

Monks, Brendan M. ^{[1
]}

Cook, Silas P. ^{[1
]}

机构：

[1] Indiana Univ, Dept Chem, Bloomington, IN 47405 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2014年 / 136卷 / 38期

关键词：

H BOND ACTIVATION; AROMATIC CARBOXAMIDES; ORTHO-ALLYLATION; DIRECT ARYLATION; METAL-COMPLEXES; ARYL PYRIDINES; HALIDES; IMINES; FUNCTIONALIZATIONS; DERIVATIVES;

D O I：

10.1021/ja506823u

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Using 8-aminoquinoline-based aryl carboxamides, the direct ortho-alkylation can be achieved in high yields in the presence of an iron source, 1,2-bis(diphenyl-phosphino)ethane (dppe) and phenylmagnesium bromide. The reactions proceed without overalkylation and provide high levels of regioselectivity. The benzylation reactions can be performed in air with reagent-grade THF, while the alkylation works well with unactivated secondary bromides and iodides in 2-methyltetrahydrofuran. Moreover, the reactions only require 5-10 min.

引用

页码：13130 / 13133

页数：4

共 50 条

[21] Iron-Catalyzed Directed Alkylation of Aromatic and Olefinic Carboxamides with Primary and Secondary Alkyl Tosylates, Mesylates, and Halides
Ilies, Laurean
Matsubara, Tatsuaki
Ichikawa, Saki
Asako, Sobi
Nakamura, Eiichi
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2014, 136 (38) : 13126 - 13129
[22] UNCATALYZED THERMAL ORTHO-ALKYLATION OF PHENOLS
GOLDSMITH, EA
SCHLATTER, MJ
TOLAND, WG
JOURNAL OF ORGANIC CHEMISTRY, 1958, 23 (12): : 1871 - 1876
[23] Optimization of phenol ortho-alkylation with styrene
P. Sh. Mamedova
V. M. Farzaliev
F. M. Velieva
E. R. Babaev
Petroleum Chemistry, 2007, 47 (1) : 55 - 60
[24] MECHANISTIC ASPECTS OF IRON-CATALYZED ALLYLIC ALKYLATION
SILVERMAN, GS
NICHOLAS, KM
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1985, 189 (APR-): : 267 - INOR
[25] Iron-catalyzed alkylation of α-oxo ketene dithioacetals
Yang, Qin
Wu, Ping
Chen, Jiping
Yu, Zhengkun
CHEMICAL COMMUNICATIONS, 2014, 50 (48) : 6337 - 6339
[26] Iron-Catalyzed Heterocycle and Arene Deprotonative Alkylation
Tran, Ly Dieu
Daugulis, Olafs
ORGANIC LETTERS, 2010, 12 (19) : 4277 - 4279
[27] Iron-catalyzed alkylation of alkenyl Grignard reagents
Cahiez, Gerard
Duplais, Christophe
Moyeux, Alban
ORGANIC LETTERS, 2007, 9 (17) : 3253 - 3254
[28] Iron-Catalyzed ortho Monoarylation of Benzamide Derivatives
Ilies, Laurean
Konno, Eita
Chen, Quan
Nakamura, Eiichi
ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2012, 1 (02) : 142 - 145
[29] Rh(III)-catalyzed ortho-Alkylation of N-Benzyltriflamides with Diazo Compounds
Han, Sang Hoon
Mishra, Neeraj Kumar
Kim, In Su
BULLETIN OF THE KOREAN CHEMICAL SOCIETY, 2015, 36 (12): : 2823 - 2828
[30] Cp*Co(<sc>iii</sc>)-catalyzed ortho-alkylation/alkenylation of anilides
Yu, Yongqi
Yu, Jiajia
Li, Yanqi
You, Mengdan
Huang, Rantao
Kong, Weiguang
Chen, Ming
Bai, Jinjin
Li, Wenguang
Li, Ting
ORGANIC & BIOMOLECULAR CHEMISTRY, 2025, 23 (09) : 2086 - 2091

← 1 2 3 4 5 →