Highly Site-Selective Metal-Free C-H Acyloxylation of Stable Enamines

Fei Wang; Wangbing Sun; Yixin Wang; Yaojia Jiang; Teck Peng Loh

doi:10.1021/acs.orglett.8b00222

Highly Site-Selective Metal-Free C-H Acyloxylation of Stable Enamines

Fei Wang, Wangbing Sun, Yixin Wang, Yaojia Jiang, Teck Peng Loh^*

^*Corresponding author for this work

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

64 Citations (Scopus)

Abstract

A highly site-selective acyloxylation of stable enamines with PhI(OAc)₂ under metal-free conditions to afford (E)-vinyl acetate derivatives in good to excellent yields is described. Depending on the judicious choice of the solvent system, either the α- or β-site-selective product could be obtained with high selectivity. For the α-site-selective product, the rearranged amide compound is obtained as the major product. This reaction proceeds under mild reaction conditions (room temperature, metal-free, and open-flask) and features a broad substrate scope.

Original language	English
Pages (from-to)	1256-1260
Number of pages	5
Journal	Organic Letters
Volume	20
Issue number	4
DOIs	https://doi.org/10.1021/acs.orglett.8b00222
Publication status	Published - Feb 16 2018
Externally published	Yes

Bibliographical note

Publisher Copyright:
© 2018 American Chemical Society.

ASJC Scopus Subject Areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

Access to Document

10.1021/acs.orglett.8b00222

Cite this

@article{92d493c1e81e40ef95be9f98b6b38d30,

title = "Highly Site-Selective Metal-Free C-H Acyloxylation of Stable Enamines",

abstract = "A highly site-selective acyloxylation of stable enamines with PhI(OAc)2 under metal-free conditions to afford (E)-vinyl acetate derivatives in good to excellent yields is described. Depending on the judicious choice of the solvent system, either the α- or β-site-selective product could be obtained with high selectivity. For the α-site-selective product, the rearranged amide compound is obtained as the major product. This reaction proceeds under mild reaction conditions (room temperature, metal-free, and open-flask) and features a broad substrate scope.",

author = "Fei Wang and Wangbing Sun and Yixin Wang and Yaojia Jiang and Loh, {Teck Peng}",

note = "Publisher Copyright: {\textcopyright} 2018 American Chemical Society.",

year = "2018",

month = feb,

day = "16",

doi = "10.1021/acs.orglett.8b00222",

language = "English",

volume = "20",

pages = "1256--1260",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

number = "4",

}

TY - JOUR

T1 - Highly Site-Selective Metal-Free C-H Acyloxylation of Stable Enamines

AU - Wang, Fei

AU - Sun, Wangbing

AU - Wang, Yixin

AU - Jiang, Yaojia

AU - Loh, Teck Peng

PY - 2018/2/16

Y1 - 2018/2/16

N2 - A highly site-selective acyloxylation of stable enamines with PhI(OAc)2 under metal-free conditions to afford (E)-vinyl acetate derivatives in good to excellent yields is described. Depending on the judicious choice of the solvent system, either the α- or β-site-selective product could be obtained with high selectivity. For the α-site-selective product, the rearranged amide compound is obtained as the major product. This reaction proceeds under mild reaction conditions (room temperature, metal-free, and open-flask) and features a broad substrate scope.

AB - A highly site-selective acyloxylation of stable enamines with PhI(OAc)2 under metal-free conditions to afford (E)-vinyl acetate derivatives in good to excellent yields is described. Depending on the judicious choice of the solvent system, either the α- or β-site-selective product could be obtained with high selectivity. For the α-site-selective product, the rearranged amide compound is obtained as the major product. This reaction proceeds under mild reaction conditions (room temperature, metal-free, and open-flask) and features a broad substrate scope.

UR - http://www.scopus.com/inward/record.url?scp=85042190799&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=85042190799&partnerID=8YFLogxK

U2 - 10.1021/acs.orglett.8b00222

DO - 10.1021/acs.orglett.8b00222

M3 - Article

C2 - 29419306

AN - SCOPUS:85042190799

SN - 1523-7060

VL - 20

SP - 1256

EP - 1260

JO - Organic Letters

JF - Organic Letters

IS - 4

ER -

Highly Site-Selective Metal-Free C-H Acyloxylation of Stable Enamines

Abstract

Bibliographical note

ASJC Scopus Subject Areas

Access to Document

Other files and links

Fingerprint

Cite this