Direct Photocatalytic Synthesis of Medium‐Sized Lactams by C−C Bond Cleavage

Reported is a novel two‐step ring‐expansion strategy for expeditious synthesis of all ring sizes of synthetically challenging (hetero)aryl‐fused medium‐sized lactams from readily available 5–8‐membered cyclic ketones. This step‐economic approach features a remote radical (hetero)aryl migration from...

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Published inAngewandte Chemie International Edition Vol. 57; no. 43; pp. 14225 - 14229
Main Authors Wang, Na, Gu, Qiang‐Shuai, Li, Zhong‐Liang, Li, Zhuang, Guo, Yu‐Long, Guo, Zhen, Liu, Xin‐Yuan
Format Journal Article
LanguageEnglish
Published WEINHEIM Wiley 22.10.2018
Wiley Subscription Services, Inc
EditionInternational ed. in English
Subjects
Aromatic compounds
Chemistry
Chemistry, Multidisciplinary
heterocycles
Ketones
medium-sized rings
Migration
photochemistry
Physical Sciences
radicals
Science & Technology
Substrates
Synthesis
CATALYSIS
medium-sized rings
radicals
RING-EXPANSION
MACROCYCLES
VISIBLE-LIGHT PHOTOREDOX
EFFICIENT SYNTHESIS
ketones
FUNCTIONALIZATION
REARRANGEMENT
heterocycles
photochemistry
CONSTRUCTION
CYCLIZATION
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Abstract Reported is a novel two‐step ring‐expansion strategy for expeditious synthesis of all ring sizes of synthetically challenging (hetero)aryl‐fused medium‐sized lactams from readily available 5–8‐membered cyclic ketones. This step‐economic approach features a remote radical (hetero)aryl migration from C to N under visible‐light conditions. Broad substrate scope, good functional‐group tolerance, high efficiency, and mild reaction conditions make this procedure very attractive. In addition, this method also provides expedient access to 13–15‐membered macrolactams upon an additional one‐step manipulation. Mechanistic studies indicate that the reaction involves an amidyl radical and is promoted by acid. Growth rings: A two‐step ring‐expansion strategy for expedient synthesis of all ring sizes of synthetically challenging (hetero)aryl‐fused medium‐sized lactams from readily available 5–8‐membered cyclic ketones has been developed. The key step involves an uncommon remote radical (hetero)aryl migration from C to N by C−C bond cleavage under irradiation with visible light.
AbstractList Reported is a novel two‐step ring‐expansion strategy for expeditious synthesis of all ring sizes of synthetically challenging (hetero)aryl‐fused medium‐sized lactams from readily available 5–8‐membered cyclic ketones. This step‐economic approach features a remote radical (hetero)aryl migration from C to N under visible‐light conditions. Broad substrate scope, good functional‐group tolerance, high efficiency, and mild reaction conditions make this procedure very attractive. In addition, this method also provides expedient access to 13–15‐membered macrolactams upon an additional one‐step manipulation. Mechanistic studies indicate that the reaction involves an amidyl radical and is promoted by acid.
Reported is a novel two-step ring-expansion strategy for expeditious synthesis of all ring sizes of synthetically challenging (hetero)aryl-fused medium-sized lactams from readily available 5-8-membered cyclic ketones. This step-economic approach features a remote radical (hetero)aryl migration from C to N under visible-light conditions. Broad substrate scope, good functional-group tolerance, high efficiency, and mild reaction conditions make this procedure very attractive. In addition, this method also provides expedient access to 13-15-membered macrolactams upon an additional one-step manipulation. Mechanistic studies indicate that the reaction involves an amidyl radical and is promoted by acid.Reported is a novel two-step ring-expansion strategy for expeditious synthesis of all ring sizes of synthetically challenging (hetero)aryl-fused medium-sized lactams from readily available 5-8-membered cyclic ketones. This step-economic approach features a remote radical (hetero)aryl migration from C to N under visible-light conditions. Broad substrate scope, good functional-group tolerance, high efficiency, and mild reaction conditions make this procedure very attractive. In addition, this method also provides expedient access to 13-15-membered macrolactams upon an additional one-step manipulation. Mechanistic studies indicate that the reaction involves an amidyl radical and is promoted by acid.
Reported is a novel two‐step ring‐expansion strategy for expeditious synthesis of all ring sizes of synthetically challenging (hetero)aryl‐fused medium‐sized lactams from readily available 5–8‐membered cyclic ketones. This step‐economic approach features a remote radical (hetero)aryl migration from C to N under visible‐light conditions. Broad substrate scope, good functional‐group tolerance, high efficiency, and mild reaction conditions make this procedure very attractive. In addition, this method also provides expedient access to 13–15‐membered macrolactams upon an additional one‐step manipulation. Mechanistic studies indicate that the reaction involves an amidyl radical and is promoted by acid. Growth rings: A two‐step ring‐expansion strategy for expedient synthesis of all ring sizes of synthetically challenging (hetero)aryl‐fused medium‐sized lactams from readily available 5–8‐membered cyclic ketones has been developed. The key step involves an uncommon remote radical (hetero)aryl migration from C to N by C−C bond cleavage under irradiation with visible light.
Author Li, Zhong‐Liang
Liu, Xin‐Yuan
Guo, Zhen
Guo, Yu‐Long
Gu, Qiang‐Shuai
Li, Zhuang
Wang, Na
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  organization: Southern University of Science and Technology
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  fullname: Li, Zhuang
  organization: Southern University of Science and Technology
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  fullname: Guo, Yu‐Long
  organization: Southern University of Science and Technology
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  surname: Liu
  fullname: Liu, Xin‐Yuan
  email: liuxy3@sustc.edu.cn
  organization: Southern University of Science and Technology
BackLink https://www.ncbi.nlm.nih.gov/pubmed/30178906$$D View this record in MEDLINE/PubMed
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Issue 43
Keywords CATALYSIS
medium-sized rings
radicals
RING-EXPANSION
MACROCYCLES
VISIBLE-LIGHT PHOTOREDOX
EFFICIENT SYNTHESIS
ketones
FUNCTIONALIZATION
REARRANGEMENT
heterocycles
photochemistry
CONSTRUCTION
CYCLIZATION
Language English
License 2018 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.
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Notes These authors contributed equally to this work.
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Snippet Reported is a novel two‐step ring‐expansion strategy for expeditious synthesis of all ring sizes of synthetically challenging (hetero)aryl‐fused medium‐sized...
Reported is a novel two-step ring-expansion strategy for expeditious synthesis of all ring sizes of synthetically challenging (hetero)aryl-fused medium-sized...
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SubjectTerms Aromatic compounds
Chemistry
Chemistry, Multidisciplinary
heterocycles
Ketones
medium-sized rings
Migration
photochemistry
Physical Sciences
radicals
Science & Technology
Substrates
Synthesis
Title Direct Photocatalytic Synthesis of Medium‐Sized Lactams by C−C Bond Cleavage
URI https://onlinelibrary.wiley.com/doi/abs/10.1002%2Fanie.201808890
http://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcApp=Summon&SrcAuth=ProQuest&DestApp=WOS&DestLinkType=FullRecord&UT=000447371500044
https://www.ncbi.nlm.nih.gov/pubmed/30178906
https://www.proquest.com/docview/2120121090
https://www.proquest.com/docview/2099434389
Volume 57
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