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Direct Use of Phosphonium Salts for Alkylation of p-Quinols: Formal α-Arylation of Carbonyls via a 5-Membered Betaine-Type Intermediate
- Source :
- Organic Letters; 20220101, Issue: Preprints
- Publication Year :
- 2022
-
Abstract
- Unlike phosphonium ylides used extensively for C═C bond formation, herein we disclose the direct use of phosphonium salts for site-selective alkylation to p-quinols via a 5-membered betaine-type intermediate. This strategy provides a novel and general approach for the synthesis of α-(m-aminoaryl) esters, amides and ketones under ambient conditions. The reaction proceeds through in situ generation of P-ylide, alkylation and aromatization. Reaction is highly compatible with diverse functional phosphonium salts and amines.
Details
- Language :
- English
- ISSN :
- 15237060 and 15237052
- Issue :
- Preprints
- Database :
- Supplemental Index
- Journal :
- Organic Letters
- Publication Type :
- Periodical
- Accession number :
- ejs60838683
- Full Text :
- https://doi.org/10.1021/acs.orglett.2c02638