Palladium-catalyzed annulation of N-alkoxy benzsulfonamides with arynes by C-H functionalization: access to dibenzosultams

Palladium-catalyzed C-H/N-H functionalization of easily prepared N-alkoxy benzsulfonamides with arynes provides dibenzosultams in good yields via C-C/C-N bond formation, accompanied by an unexpected N-O bond cleavage. A mechanistic study shows that the reaction proceeds through a rate-determining C-...

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Published inORGANIC CHEMISTRY FRONTIERS Vol. 6; no. 4; pp. 517 - 522
Main Authors Feng, Simin, Li, Shan, Li, Jing, Wei, Junfa
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 21.02.2019
Royal Society of Chemistry
Subjects
Chemical reactions
Chemistry
Chemistry, Organic
Cleavage
Hydrogen bonds
Organic chemistry
Palladium
Physical Sciences
Science & Technology
IN-VITRO
INTRAMOLECULAR ARYLATION
EMPLOYING ARYNES
EFFICIENT SYNTHESIS
ARYL SULFONAMIDES
BOND FORMATION
OXIDATIVE ANNULATION
ISOQUINOLONE SYNTHESIS
TRANSITION-METAL-FREE
CYCLIC SULFONAMIDES
Online AccessGet full text
ISSN2052-4129
2052-4110
2052-4110
DOI10.1039/c8qo01311j

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Abstract Palladium-catalyzed C-H/N-H functionalization of easily prepared N-alkoxy benzsulfonamides with arynes provides dibenzosultams in good yields via C-C/C-N bond formation, accompanied by an unexpected N-O bond cleavage. A mechanistic study shows that the reaction proceeds through a rate-determining C-H bond cleavage.
AbstractList Palladium-catalyzed C–H/N–H functionalization of easily prepared N-alkoxy benzsulfonamides with arynes provides dibenzosultams in good yields via C–C/C–N bond formation, accompanied by an unexpected N–O bond cleavage. A mechanistic study shows that the reaction proceeds through a rate-determining C–H bond cleavage.
Author Wei, Junfa
Li, Jing
Feng, Simin
Li, Shan
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  surname: Wei
  fullname: Wei, Junfa
  email: weijf@snnu.edu.cn
  organization: Shaanxi Normal Univ, Sch Chem & Chem Engn, Xian 710119, Shaanxi, Peoples R China
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Keywords IN-VITRO
INTRAMOLECULAR ARYLATION
EMPLOYING ARYNES
EFFICIENT SYNTHESIS
ARYL SULFONAMIDES
BOND FORMATION
OXIDATIVE ANNULATION
ISOQUINOLONE SYNTHESIS
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Snippet Palladium-catalyzed C-H/N-H functionalization of easily prepared N-alkoxy benzsulfonamides with arynes provides dibenzosultams in good yields via C-C/C-N bond...
Palladium-catalyzed C–H/N–H functionalization of easily prepared N-alkoxy benzsulfonamides with arynes provides dibenzosultams in good yields via C–C/C–N bond...
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SubjectTerms Chemical reactions
Chemistry
Chemistry, Organic
Cleavage
Hydrogen bonds
Organic chemistry
Palladium
Physical Sciences
Science & Technology
Title Palladium-catalyzed annulation of N-alkoxy benzsulfonamides with arynes by C-H functionalization: access to dibenzosultams
URI http://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcApp=Summon&SrcAuth=ProQuest&DestApp=WOS&DestLinkType=FullRecord&UT=000458518400014
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