Photoredox/Cobalt-Catalyzed Phosphinyloxy Radical Addition/Cyclization Cascade: Synthesis of Phosphaisocoumarins

A novel visible-light photoredox-catalyzed phosphinyloxy radical addition/cyclization cascade of arylphosphinic acids or arylphosphonic acid monoesters with alkynes has been developed, which provides an efficient and practical access to various phosphaisocoumarins by using a dual catalytic system co...

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Bibliographic Details
Published inJournal of organic chemistry Vol. 84; no. 11; pp. 6798 - 6806
Main Authors Qiao, Ming-Ming, Liu, Yi-Yin, Yao, Sheng, Ma, Tian-Cong, Tang, Zi-Long, Shi, De-Qing, Xiao, Wen-Jing
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 07.06.2019
Amer Chemical Soc
Subjects
acids
alkynes
ambient temperature
catalysts
chemical structure
Chemistry
Chemistry, Organic
cobalt
cyclization reactions
esters
light
organic chemistry
oxidants
photosensitizing agents
Physical Sciences
Science & Technology
ACID
HYDROGENATION
LIGANDS
BONDS
ALKYNES
EFFICIENT
CYCLIZATION
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ISSN0022-3263
1520-6904
1520-6904
DOI10.1021/acs.joc.9b00570

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Summary:A novel visible-light photoredox-catalyzed phosphinyloxy radical addition/cyclization cascade of arylphosphinic acids or arylphosphonic acid monoesters with alkynes has been developed, which provides an efficient and practical access to various phosphaisocoumarins by using a dual catalytic system containing an acridinium photosensitizer and a cobaloxime proton-reducing catalyst [Co­(dmgH)2]­PyCl at ambient temperature. This method has advantages of a broad substrate scope, mild condition, as well as no sacrificial oxidant.
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ISSN:0022-3263
1520-6904
1520-6904
DOI:10.1021/acs.joc.9b00570