Ni-Catalyzed cross-coupling reactions of N-acylpyrrole-type amides with organoboron reagents

The catalytic conversion of amides to ketones is highly desirable yet challenging in organic synthesis. We herein report the first Ni/bisNHC-catalyzed cross-coupling of N-acylpyrrole-type amides with arylboronic esters to obtain diarylketones. This method is facilitated by a new chelating bis-NHC li...

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Published inChemical communications (Cambridge, England) Vol. 53; no. 93; pp. 12584 - 12587
Main Authors Huang, Pei-Qiang, Chen, Hang
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 2017
Royal Society of Chemistry
Subjects
Amides
Catalytic converters
Chelation
Chemical reactions
Chemical synthesis
Chemistry
Chemistry, Multidisciplinary
Coupling
Cross coupling
Esters
Functional groups
Ketones
Physical Sciences
Reagents
Science & Technology
MECHANISTIC ASPECTS
ACTIVATION
REDUCTIVE NUCLEOPHILIC-ADDITION
ORGANOMETALLIC REAGENTS
SECONDARY AMIDES
NICKEL CATALYSIS
ALKYLATION
BOND FORMATION
HETEROCYCLIC CARBENES
ENANTIOSELECTIVE TOTAL-SYNTHESIS
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Summary:The catalytic conversion of amides to ketones is highly desirable yet challenging in organic synthesis. We herein report the first Ni/bisNHC-catalyzed cross-coupling of N-acylpyrrole-type amides with arylboronic esters to obtain diarylketones. This method is facilitated by a new chelating bis-NHC ligand. The reaction tolerates diverse functional groups on both arylamide and arylboronic ester partners including sensitive ester and ketone groups.
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ISSN:1359-7345
1364-548X
DOI:10.1039/c7cc07457c