FeCl3-catalyzed selective acylation of amines with 1,3-diketones via C-C bond cleavage

Sinan Wang; Yang Yu; Xuyun Chen; Haipan Zhu; Peile Du; Guohua Liu; Liguang Lou; Hao Li; Wei Wang

doi:10.1016/j.tetlet.2014.12.146

FeCl₃-catalyzed selective acylation of amines with 1,3-diketones via C-C bond cleavage

Sinan Wang, Yang Yu, Xuyun Chen, Haipan Zhu, Peile Du, Guohua Liu, Liguang Lou, Hao Li, Wei Wang

Research output: Contribution to journal › Article › peer-review

21 Scopus citations

Abstract

We describe a novel FeCl₃ catalyzed selective acylation of amines involving the C-C bond cleavage of simple 1,3-diketones. The process proceeds efficiently under a neat condition to give structurally diverse amides. Notably, the acylation process displays high selectivity toward amines over hydroxyl functionality. Traditionally difficult aromatic amines and sterically demanding disubstituted amines can engage in the process with high efficiency.

Original language	English (US)
Pages (from-to)	3093-3096
Number of pages	4
Journal	Tetrahedron Letters
Volume	56
Issue number	23
DOIs	https://doi.org/10.1016/j.tetlet.2014.12.146
State	Published - May 25 2015
Externally published	Yes

Keywords

1,3-Diketones
Acylation
C-C bond cleavage
FeCl

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

Access to Document

10.1016/j.tetlet.2014.12.146

Cite this

@article{dac0a54874924e4c8eb6d3f6aecadfef,

title = "FeCl3-catalyzed selective acylation of amines with 1,3-diketones via C-C bond cleavage",

abstract = "We describe a novel FeCl3 catalyzed selective acylation of amines involving the C-C bond cleavage of simple 1,3-diketones. The process proceeds efficiently under a neat condition to give structurally diverse amides. Notably, the acylation process displays high selectivity toward amines over hydroxyl functionality. Traditionally difficult aromatic amines and sterically demanding disubstituted amines can engage in the process with high efficiency.",

keywords = "1,3-Diketones, Acylation, C-C bond cleavage, FeCl",

author = "Sinan Wang and Yang Yu and Xuyun Chen and Haipan Zhu and Peile Du and Guohua Liu and Liguang Lou and Hao Li and Wei Wang",

note = "Funding Information: Financial support from the Program for Professor of Special Appointment (Eastern Scholar) (No. 201226, H.L.), the National Science Foundation of China (No. 21372073, W.W.), the Fundamental Research Funds for the Central Universities and East China University of Science and Technology (start-up fund, H.L. and W.W.) is gratefully acknowledged. Publisher Copyright: {\textcopyright} 2015 Elsevier Ltd All rights reserved.",

year = "2015",

month = may,

day = "25",

doi = "10.1016/j.tetlet.2014.12.146",

language = "English (US)",

volume = "56",

pages = "3093--3096",

journal = "Tetrahedron Letters",

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TY - JOUR

T1 - FeCl3-catalyzed selective acylation of amines with 1,3-diketones via C-C bond cleavage

AU - Wang, Sinan

AU - Yu, Yang

AU - Chen, Xuyun

AU - Zhu, Haipan

AU - Du, Peile

AU - Liu, Guohua

AU - Lou, Liguang

AU - Li, Hao

AU - Wang, Wei

N1 - Funding Information: Financial support from the Program for Professor of Special Appointment (Eastern Scholar) (No. 201226, H.L.), the National Science Foundation of China (No. 21372073, W.W.), the Fundamental Research Funds for the Central Universities and East China University of Science and Technology (start-up fund, H.L. and W.W.) is gratefully acknowledged. Publisher Copyright: © 2015 Elsevier Ltd All rights reserved.

PY - 2015/5/25

Y1 - 2015/5/25

N2 - We describe a novel FeCl3 catalyzed selective acylation of amines involving the C-C bond cleavage of simple 1,3-diketones. The process proceeds efficiently under a neat condition to give structurally diverse amides. Notably, the acylation process displays high selectivity toward amines over hydroxyl functionality. Traditionally difficult aromatic amines and sterically demanding disubstituted amines can engage in the process with high efficiency.

AB - We describe a novel FeCl3 catalyzed selective acylation of amines involving the C-C bond cleavage of simple 1,3-diketones. The process proceeds efficiently under a neat condition to give structurally diverse amides. Notably, the acylation process displays high selectivity toward amines over hydroxyl functionality. Traditionally difficult aromatic amines and sterically demanding disubstituted amines can engage in the process with high efficiency.

KW - 1,3-Diketones

KW - Acylation

KW - C-C bond cleavage

KW - FeCl

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