Intermolecular sp3 C-H bond functionalization of alkyl amides as a new method for the one-pot synthesis of functional neo alkyl amides with remote functional groups

被引：5

作者：

Akhrem, Irena S. ^{[1
]}

Avetisyan, Dzhul'etta V. ^{[1
]}

Afanas'eva, Lyudmila V. ^{[1
]}

Artyushin, Oleg I. ^{[1
]}

Kagramanov, Nikolai D. ^{[1
]}

机构：

[1] Russian Acad Sci, AN Nesmeyanov Inst Organoelement Cpds, Moscow 119991, Russia

来源：

TETRAHEDRON LETTERS | 2015年 / 56卷 / 03期

基金：

俄罗斯基础研究基金会;

关键词：

Amides; sp(3) C-H bond remote functionalization; Amide cyclization; Carbonylation; Superelectrophiles; ORTHO-ARYLATION; ACIDS; KETONES; ALKANE; SUPERACIDS; ALCOHOLS;

D O I：

10.1016/j.tetlet.2014.11.115

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The one-pot, regioselective, remote functionalization of amides of octanoic acid [R2NCOC7H15, NR2 = NH2, NEt2, NC4H8O, (morpholinyl)] via Csp(3)-H bond cleavage with CO and various nucleophiles (EtOH, (PrOH)-Pr-i, CF3CH2OH, H(CF2)(2)CH2OH, C8F17SH, Et2NH, morpholine, furan, thiophene, and anisole) in the presence of the superelectrophilic complex, CBr4 center dot 2AlBr(3) has been performed for the first time. This methodology provides access to new synthetically challenging and promising derivatives of amides with remote functional groups of neo-structure. The oxidative cyclization of octanamide into a six-membered cyclic amide with the C(Me)Et group adjacent to the heteroatom using CBr4 center dot 2AlBr(3) has been demonstrated. (C) 2014 Elsevier Ltd. All rights reserved.

引用

页码：562 / 566

页数：5

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