Catalyst-free thiophosphorylation of in situ formed ortho-quinone methides

A metal-, chloride reagent and base-free thiophosphorylation reaction of in situ formed ortho-quinone methide (o-QM) to synthesize functionalized thiophosphates has been developed. The reaction is an atom-economical process, producing water as the sole byproduct. (EtO)(2)P(O)SH functions as both a B...

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Bibliographic Details
Published inOrganic & biomolecular chemistry Vol. 21; no. 11; pp. 2370 - 2374
Main Authors Ash, Jeffrey, Kang, Jun Yong
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 15.03.2023
Royal Society of Chemistry
Subjects
Catalysts
Chemistry
Chemistry, Organic
Physical Sciences
Quinones
Reagents
Science & Technology
Thiophosphate
THIOLS
PHOSPHONATES
PROMOTED SYNTHESIS
THIOPHOSPHATES
PHOSPHOROTHIOLATION
P(O)H COMPOUNDS
GENERATION
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Summary:A metal-, chloride reagent and base-free thiophosphorylation reaction of in situ formed ortho-quinone methide (o-QM) to synthesize functionalized thiophosphates has been developed. The reaction is an atom-economical process, producing water as the sole byproduct. (EtO)(2)P(O)SH functions as both a Bronsted acid and nucleophilic thiolate to produce the o-QM intermediate and the thiophosphate product, respectively. The aza o-QMs were also successfully thiophosphorylated in the presence of catalytic TsOH to form sulfonamido thiophosphates.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
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ISSN:1477-0520
1477-0539
DOI:10.1039/d2ob02169b