Deaminative (Carbonylative) Alkyl‐Heck‐type Reactions Enabled by Photocatalytic C−N Bond Activation

The palladium‐catalyzed Heck reaction is a well‐known, Nobel Prize winning transformation for producing alkenes. Unlike the alkenyl and aryl variants of the Heck reaction, the alkyl‐Heck reaction is still underdeveloped owing to the competitive side reactions of alkyl–palladium species. Herein, we d...

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Published inAngewandte Chemie International Edition Vol. 58; no. 8; pp. 2402 - 2406
Main Authors Jiang, Xuan, Zhang, Mao‐Mao, Xiong, Wei, Lu, Liang‐Qiu, Xiao, Wen‐Jing
Format Journal Article
LanguageEnglish
Published WEINHEIM Wiley 18.02.2019
Wiley Subscription Services, Inc
EditionInternational ed. in English
Subjects
Activation
Aliphatic compounds
Alkenes
Amines
Aromatic compounds
carbonylative reactions
Carbonyls
Catalysis
Chemical reactions
Chemistry
Chemistry, Multidisciplinary
deaminative transformations
Genetic transformation
Heck reaction
Palladium
photocatalysis
Photoredox catalysis
Physical Sciences
Science & Technology
Side reactions
HALIDES
ROOM-TEMPERATURE
carbonylative reactions
amines
deaminative transformations
Heck reaction
BENZYLIC AMINES
FUNCTIONALIZATION
CROSS-COUPLINGS
OLEFINS
GENERATION
ARYL
photocatalysis
METAL-FREE
TRANSFORMATIONS
Online AccessGet full text

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Abstract The palladium‐catalyzed Heck reaction is a well‐known, Nobel Prize winning transformation for producing alkenes. Unlike the alkenyl and aryl variants of the Heck reaction, the alkyl‐Heck reaction is still underdeveloped owing to the competitive side reactions of alkyl–palladium species. Herein, we describe the development of a deaminative alkyl‐Heck‐type reaction that proceeds through C−N bond activation by visible‐light photoredox catalysis. A variety of aliphatic primary amines were found to be efficient starting materials for this new process, affording the corresponding alkene products in good yields under mild reaction conditions. Moreover, this strategy was successfully applied to deaminative carbonylative alkyl‐Heck‐type reactions. Single‐electron process: A deaminative alkyl‐Heck‐type reaction and its carbonylative variant proceed through photocatalytic C−N bond activation. This process represents a significant complement to the classic palladium‐catalyzed Heck reaction, and features easily available starting materials, good reaction efficiency, and mild reaction conditions. Tppy=2,4,6‐triphenylpyridine.
AbstractList The palladium-catalyzed Heck reaction is a well-known, Nobel Prize winning transformation for producing alkenes. Unlike the alkenyl and aryl variants of the Heck reaction, the alkyl-Heck reaction is still underdeveloped owing to the competitive side reactions of alkyl-palladium species. Herein, we describe the development of a deaminative alkyl-Heck-type reaction that proceeds through C-N bond activation by visible-light photoredox catalysis. A variety of aliphatic primary amines were found to be efficient starting materials for this new process, affording the corresponding alkene products in good yields under mild reaction conditions. Moreover, this strategy was successfully applied to deaminative carbonylative alkyl-Heck-type reactions.
The palladium‐catalyzed Heck reaction is a well‐known, Nobel Prize winning transformation for producing alkenes. Unlike the alkenyl and aryl variants of the Heck reaction, the alkyl‐Heck reaction is still underdeveloped owing to the competitive side reactions of alkyl–palladium species. Herein, we describe the development of a deaminative alkyl‐Heck‐type reaction that proceeds through C−N bond activation by visible‐light photoredox catalysis. A variety of aliphatic primary amines were found to be efficient starting materials for this new process, affording the corresponding alkene products in good yields under mild reaction conditions. Moreover, this strategy was successfully applied to deaminative carbonylative alkyl‐Heck‐type reactions.
The palladium‐catalyzed Heck reaction is a well‐known, Nobel Prize winning transformation for producing alkenes. Unlike the alkenyl and aryl variants of the Heck reaction, the alkyl‐Heck reaction is still underdeveloped owing to the competitive side reactions of alkyl–palladium species. Herein, we describe the development of a deaminative alkyl‐Heck‐type reaction that proceeds through C−N bond activation by visible‐light photoredox catalysis. A variety of aliphatic primary amines were found to be efficient starting materials for this new process, affording the corresponding alkene products in good yields under mild reaction conditions. Moreover, this strategy was successfully applied to deaminative carbonylative alkyl‐Heck‐type reactions. Single‐electron process: A deaminative alkyl‐Heck‐type reaction and its carbonylative variant proceed through photocatalytic C−N bond activation. This process represents a significant complement to the classic palladium‐catalyzed Heck reaction, and features easily available starting materials, good reaction efficiency, and mild reaction conditions. Tppy=2,4,6‐triphenylpyridine.
Abstract The palladium‐catalyzed Heck reaction is a well‐known, Nobel Prize winning transformation for producing alkenes. Unlike the alkenyl and aryl variants of the Heck reaction, the alkyl‐Heck reaction is still underdeveloped owing to the competitive side reactions of alkyl–palladium species. Herein, we describe the development of a deaminative alkyl‐Heck‐type reaction that proceeds through C−N bond activation by visible‐light photoredox catalysis. A variety of aliphatic primary amines were found to be efficient starting materials for this new process, affording the corresponding alkene products in good yields under mild reaction conditions. Moreover, this strategy was successfully applied to deaminative carbonylative alkyl‐Heck‐type reactions.
Author Lu, Liang‐Qiu
Zhang, Mao‐Mao
Xiao, Wen‐Jing
Jiang, Xuan
Xiong, Wei
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  organization: Central China Normal University
– sequence: 2
  givenname: Mao‐Mao
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  fullname: Zhang, Mao‐Mao
  organization: Central China Normal University
– sequence: 3
  givenname: Wei
  surname: Xiong
  fullname: Xiong, Wei
  organization: Central China Normal University
– sequence: 4
  givenname: Liang‐Qiu
  surname: Lu
  fullname: Lu, Liang‐Qiu
  email: luliangqiu@mail.ccnu.edu.cn
  organization: Central China Normal University
– sequence: 5
  givenname: Wen‐Jing
  orcidid: 0000-0002-9318-6021
  surname: Xiao
  fullname: Xiao, Wen‐Jing
  email: wxiao@mail.ccnu.edu.cn
  organization: Chinese Academy of Sciences
BackLink https://www.ncbi.nlm.nih.gov/pubmed/30565825$$D View this record in MEDLINE/PubMed
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Issue 8
Keywords HALIDES
ROOM-TEMPERATURE
carbonylative reactions
amines
deaminative transformations
Heck reaction
BENZYLIC AMINES
FUNCTIONALIZATION
CROSS-COUPLINGS
OLEFINS
GENERATION
ARYL
photocatalysis
METAL-FREE
TRANSFORMATIONS
Language English
License 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.
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Snippet The palladium‐catalyzed Heck reaction is a well‐known, Nobel Prize winning transformation for producing alkenes. Unlike the alkenyl and aryl variants of the...
The palladium-catalyzed Heck reaction is a well-known, Nobel Prize winning transformation for producing alkenes. Unlike the alkenyl and aryl variants of the...
Abstract The palladium‐catalyzed Heck reaction is a well‐known, Nobel Prize winning transformation for producing alkenes. Unlike the alkenyl and aryl variants...
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SubjectTerms Activation
Aliphatic compounds
Alkenes
Amines
Aromatic compounds
carbonylative reactions
Carbonyls
Catalysis
Chemical reactions
Chemistry
Chemistry, Multidisciplinary
deaminative transformations
Genetic transformation
Heck reaction
Palladium
photocatalysis
Photoredox catalysis
Physical Sciences
Science & Technology
Side reactions
Title Deaminative (Carbonylative) Alkyl‐Heck‐type Reactions Enabled by Photocatalytic C−N Bond Activation
URI https://onlinelibrary.wiley.com/doi/abs/10.1002%2Fanie.201813689
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https://www.ncbi.nlm.nih.gov/pubmed/30565825
https://www.proquest.com/docview/2178166426
https://search.proquest.com/docview/2158557608
Volume 58
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