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Cobalt-catalyzed oxidative esterification of allylic/benzylic C(sp(3))-H bonds
Ren, Tian-Lu1,2; Xu, Bao-Hua1,2; Mahmood, Sajid1,2; Sun, Ming-Xue3; Zhang, Suo-Jiang1,2
2017-05-18
Source PublicationTETRAHEDRON
ISSN0040-4020
Volume73Issue:20Pages:2943-2948
Abstract

A protocol for the cobalt-catalyzed oxidative esterification of allylic/benzylic C(sp(3))-H bonds with carboxylic acids was developed in this work. Mechanistic studies revealed that C(sp(3))-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 beta-damascenone that avoided the use of NBS. (C) 2017 Elsevier Ltd. All rights reserved.

KeywordCobalt Oxidative Esterification c(Sp(3))-h Bond Activation Carboxylic Acid Peroxide
SubtypeArticle
WOS HeadingsScience & Technology ; Physical Sciences
DOI10.1016/j.tet.2017.04.002
Indexed BySCI
Language英语
WOS KeywordMetal-free Conditions ; Allylic Oxidation ; Butyl Hydroperoxide ; Aromatic-aldehydes ; Carboxylic-acids ; Beta-damascenone ; Benzylic Esters ; Cyclic Ethers ; Olefins ; Activation
WOS Research AreaChemistry
WOS SubjectChemistry, Organic
Funding OrganizationNational Key Projects for Fundamental Research and Development of China(2016YFB0601303) ; National Natural Science Foundation of China(21476240) ; Key Program of National Natural Science Foundation of China(91434203) ; Instrument Developing Project of the Chinese Academy of Sciences(YZ201521) ; CAS (Chinese Academy of Sciences) 100-Talent Program
WOS IDWOS:000401210200012
Citation statistics
Document Type期刊论文
Identifierhttp://ir.ipe.ac.cn/handle/122111/22537
Collection多相复杂系统国家重点实验室
Affiliation1.Chinese Acad Sci, Inst Proc Engn, State Key Lab Multiphase Complex Syst, Key Lab Green Proc & Engn,Beijing Key Lab Ion Liq, Beijing 100190, Peoples R China
2.Univ Chinese Acad Sci, Sch Chem & Chem Engn, Beijing 100049, Peoples R China
3.Henan Univ, Henan Engn Res Ctr Resource & Energy Recovery Was, Coll Chem & Chem Engn, Kaifeng 475004, Peoples R China
Recommended Citation
GB/T 7714
Ren, Tian-Lu,Xu, Bao-Hua,Mahmood, Sajid,et al. Cobalt-catalyzed oxidative esterification of allylic/benzylic C(sp(3))-H bonds[J]. TETRAHEDRON,2017,73(20):2943-2948.
APA Ren, Tian-Lu,Xu, Bao-Hua,Mahmood, Sajid,Sun, Ming-Xue,&Zhang, Suo-Jiang.(2017).Cobalt-catalyzed oxidative esterification of allylic/benzylic C(sp(3))-H bonds.TETRAHEDRON,73(20),2943-2948.
MLA Ren, Tian-Lu,et al."Cobalt-catalyzed oxidative esterification of allylic/benzylic C(sp(3))-H bonds".TETRAHEDRON 73.20(2017):2943-2948.
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