Copper/Manganese Cocatalyzed Oxidative Coupling of Vinylarenes with Ketones

A novel copper/manganese cocatalyzed direct oxidative coupling of terminal vinylarenes with ketones via C­(sp3)–H bond functionalization following C–C bond formation has been developed using tert-butyl hydroperoxide as the radical initiator. Various ketones underwent a free-radical addition of termi...

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Published inOrganic letters Vol. 17; no. 18; pp. 4460 - 4463
Main Authors Lan, Xing-Wang, Wang, Nai-Xing, Zhang, Wei, Wen, Jia-Long, Bai, Cui-Bing, Xing, Yalan, Li, Yi-He
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 18.09.2015
Amer Chemical Soc
Subjects
chemical bonding
chemical reactions
chemical structure
Chemistry
Chemistry, Organic
copper
ketones
manganese
Physical Sciences
reaction mechanisms
regioselectivity
Science & Technology
FUNCTIONALIZATION
SP C-H
SODIUM TRIFLUOROMETHANESULFINATE
1,4-DICARBONYL COMPOUNDS
SIMPLE ALKANES
ALKYL NITRILES
OLEFINS
CYCLIC ETHERS
METAL-FREE
UNACTIVATED ALKENES
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Abstract A novel copper/manganese cocatalyzed direct oxidative coupling of terminal vinylarenes with ketones via C­(sp3)–H bond functionalization following C–C bond formation has been developed using tert-butyl hydroperoxide as the radical initiator. Various ketones underwent a free-radical addition of terminal vinylarenes to give the corresponding 1,4-dicarbonyl products with excellent regioselectivity and efficiency through one step. A possible reaction mechanism has been proposed.
AbstractList A novel copper/manganese cocatalyzed direct oxidative coupling of terminal vinylarenes with ketones via C(sp(3))-H bond functionalization following C-C bond formation has been developed using tert-butyl hydroperoxide as the radical initiator. Various ketones underwent a free-radical addition of terminal vinylarenes to give the corresponding 1,4-dicarbonyl products with excellent regioselectivity and efficiency through one step. A possible reaction mechanism has been proposed.A novel copper/manganese cocatalyzed direct oxidative coupling of terminal vinylarenes with ketones via C(sp(3))-H bond functionalization following C-C bond formation has been developed using tert-butyl hydroperoxide as the radical initiator. Various ketones underwent a free-radical addition of terminal vinylarenes to give the corresponding 1,4-dicarbonyl products with excellent regioselectivity and efficiency through one step. A possible reaction mechanism has been proposed.
A novel copper/manganese cocatalyzed direct oxidative coupling of terminal vinylarenes with ketones via C(sp³)–H bond functionalization following C–C bond formation has been developed using tert-butyl hydroperoxide as the radical initiator. Various ketones underwent a free-radical addition of terminal vinylarenes to give the corresponding 1,4-dicarbonyl products with excellent regioselectivity and efficiency through one step. A possible reaction mechanism has been proposed.
A novel copper/manganese cocatalyzed direct oxidative coupling of terminal vinylarenes with ketones via C(sp(3))-H bond functionalization following C-C bond formation has been developed using tert-butyl hydroperoxide as the radical initiator. Various ketones underwent a free-radical addition of terminal vinylarenes to give the corresponding 1,4-dicarbonyl products with excellent regioselectivity and efficiency through one step. A possible reaction mechanism has been proposed.
A novel copper/manganese cocatalyzed direct oxidative coupling of terminal vinylarenes with ketones via C­(sp3)–H bond functionalization following C–C bond formation has been developed using tert-butyl hydroperoxide as the radical initiator. Various ketones underwent a free-radical addition of terminal vinylarenes to give the corresponding 1,4-dicarbonyl products with excellent regioselectivity and efficiency through one step. A possible reaction mechanism has been proposed.
Author Wen, Jia-Long
Bai, Cui-Bing
Zhang, Wei
Li, Yi-He
Wang, Nai-Xing
Lan, Xing-Wang
Xing, Yalan
AuthorAffiliation Department of Chemistry
Chinese Academy of Sciences
Technical Institute of Physics and Chemistry
William Paterson University of New Jersey
AuthorAffiliation_xml – name: Department of Chemistry
– name: Technical Institute of Physics and Chemistry
– name: Chinese Academy of Sciences
– name: William Paterson University of New Jersey
Author_xml – sequence: 1
  givenname: Xing-Wang
  surname: Lan
  fullname: Lan, Xing-Wang
– sequence: 2
  givenname: Nai-Xing
  surname: Wang
  fullname: Wang, Nai-Xing
  email: nxwang@mail.ipc.ac.cn
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  fullname: Li, Yi-He
BackLink https://www.ncbi.nlm.nih.gov/pubmed/26348870$$D View this record in MEDLINE/PubMed
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Keywords FUNCTIONALIZATION
SP C-H
SODIUM TRIFLUOROMETHANESULFINATE
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SIMPLE ALKANES
ALKYL NITRILES
OLEFINS
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Snippet A novel copper/manganese cocatalyzed direct oxidative coupling of terminal vinylarenes with ketones via C­(sp3)–H bond functionalization following C–C bond...
A novel copper/manganese cocatalyzed direct oxidative coupling of terminal vinylarenes with ketones via C(sp(3))-H bond functionalization following C-C bond...
A novel copper/manganese cocatalyzed direct oxidative coupling of terminal vinylarenes with ketones via C(sp³)–H bond functionalization following C–C bond...
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SubjectTerms chemical bonding
chemical reactions
chemical structure
Chemistry
Chemistry, Organic
copper
ketones
manganese
Physical Sciences
reaction mechanisms
regioselectivity
Science & Technology
Title Copper/Manganese Cocatalyzed Oxidative Coupling of Vinylarenes with Ketones
URI http://dx.doi.org/10.1021/acs.orglett.5b02116
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https://www.proquest.com/docview/2020863270
Volume 17
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