Autoxidative C(sp 2)–P Formation: Direct Phosphorylation of Heteroarenes under Oxygen, Metal-Free, and Solvent-Free Conditions

We reveal here a direct autoxidative phosphorylation of heteroarenes induced by oxygen under metal-free and solvent-free conditions. This new methodology provides an economical, operationally simple, and environmentally friendly approach toward (Het)­C­(sp 2)–P formation with medium to excellent yie...

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Published inJournal of organic chemistry Vol. 81; no. 11; pp. 4682 - 4689
Main Authors Luo, Kai, Chen, Yao-Zhong, Chen, Li-Xian, Wu, Lei
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 03.06.2016
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
FUNCTIONALIZATION
C-H BOND
ARYL MESYLATES
OXIDATIVE ACTIVATION
ARYLATION
STEREOSELECTIVE-SYNTHESIS
PALLADIUM-CATALYZED PHOSPHONATION
FORMING REACTIONS
EFFICIENT
MOLECULAR-OXYGEN
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Summary:We reveal here a direct autoxidative phosphorylation of heteroarenes induced by oxygen under metal-free and solvent-free conditions. This new methodology provides an economical, operationally simple, and environmentally friendly approach toward (Het)­C­(sp 2)–P formation with medium to excellent yields. Heteroarenes including thiazole and quinoxaline derivatives are applicable under standard conditions, which is testified via a radical mechanism.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
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ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.6b00592