Cobalt-catalyzed oxidative esterification of allylic/benzylic C(sp3)–H bonds

Tian Lu Ren; Bao Hua Xu; Sajid Mahmood; Ming Xue Sun; Suo Jiang Zhang

doi:10.1016/j.tet.2017.04.002

Cobalt-catalyzed oxidative esterification of allylic/benzylic C(sp³)–H bonds

Tian Lu Ren
, Bao Hua Xu^*
, Sajid Mahmood
, Ming Xue Sun
, Suo Jiang Zhang

^*Corresponding author for this work

CAS - Institute of Process Engineering
University of Chinese Academy of Sciences
Henan University

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

20 Citations (Scopus)

Abstract

A protocol for the cobalt-catalyzed oxidative esterification of allylic/benzylic C(sp³)–H bonds with carboxylic acids was developed in this work. Mechanistic studies revealed that C(sp³)–H bond activation in the hydrocarbon was the turnover-limiting step and the in-situ formed [Co(III)]Ot-Bu did not engage in hydrogen atom abstraction (HAA) of a C–H bond. This protocol was successfully incorporated into a synthetic pathway to β-damascenone that avoided the use of NBS.

Original language	English
Pages (from-to)	2943-2948
Number of pages	6
Journal	Tetrahedron
Volume	73
Issue number	20
DOIs	https://doi.org/10.1016/j.tet.2017.04.002
Publication status	Published - 2017
Externally published	Yes

Keywords

C(sp)–H bond activation
Carboxylic acid
Cobalt
Oxidative esterification
Peroxide

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10.1016/j.tet.2017.04.002

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title = "Cobalt-catalyzed oxidative esterification of allylic/benzylic C(sp3)–H bonds",

abstract = "A protocol for the cobalt-catalyzed oxidative esterification of allylic/benzylic C(sp3)–H bonds with carboxylic acids was developed in this work. Mechanistic studies revealed that C(sp3)–H bond activation in the hydrocarbon was the turnover-limiting step and the in-situ formed [Co(III)]Ot-Bu did not engage in hydrogen atom abstraction (HAA) of a C–H bond. This protocol was successfully incorporated into a synthetic pathway to β-damascenone that avoided the use of NBS.",

keywords = "C(sp)–H bond activation, Carboxylic acid, Cobalt, Oxidative esterification, Peroxide",

author = "Ren, \{Tian Lu\} and Xu, \{Bao Hua\} and Sajid Mahmood and Sun, \{Ming Xue\} and Zhang, \{Suo Jiang\}",

note = "Publisher Copyright: {\textcopyright} 2017 Elsevier Ltd",

year = "2017",

doi = "10.1016/j.tet.2017.04.002",

language = "English",

volume = "73",

pages = "2943--2948",

journal = "Tetrahedron",

issn = "0040-4020",

publisher = "Elsevier Ltd.",

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TY - JOUR

T1 - Cobalt-catalyzed oxidative esterification of allylic/benzylic C(sp3)–H bonds

AU - Ren, Tian Lu

AU - Xu, Bao Hua

AU - Mahmood, Sajid

AU - Sun, Ming Xue

AU - Zhang, Suo Jiang

PY - 2017

Y1 - 2017

N2 - A protocol for the cobalt-catalyzed oxidative esterification of allylic/benzylic C(sp3)–H bonds with carboxylic acids was developed in this work. Mechanistic studies revealed that C(sp3)–H bond activation in the hydrocarbon was the turnover-limiting step and the in-situ formed [Co(III)]Ot-Bu did not engage in hydrogen atom abstraction (HAA) of a C–H bond. This protocol was successfully incorporated into a synthetic pathway to β-damascenone that avoided the use of NBS.

AB - A protocol for the cobalt-catalyzed oxidative esterification of allylic/benzylic C(sp3)–H bonds with carboxylic acids was developed in this work. Mechanistic studies revealed that C(sp3)–H bond activation in the hydrocarbon was the turnover-limiting step and the in-situ formed [Co(III)]Ot-Bu did not engage in hydrogen atom abstraction (HAA) of a C–H bond. This protocol was successfully incorporated into a synthetic pathway to β-damascenone that avoided the use of NBS.

KW - C(sp)–H bond activation

KW - Carboxylic acid

KW - Cobalt

KW - Oxidative esterification

KW - Peroxide

UR - https://www.scopus.com/pages/publications/85017147821

U2 - 10.1016/j.tet.2017.04.002

DO - 10.1016/j.tet.2017.04.002

M3 - Article

AN - SCOPUS:85017147821

SN - 0040-4020

VL - 73

SP - 2943

EP - 2948

JO - Tetrahedron

JF - Tetrahedron

IS - 20

ER -

Cobalt-catalyzed oxidative esterification of allylic/benzylic C(sp³)–H bonds

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Keywords

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