Hydro/Fluoro-phosphoro(di)thiolation of Allenamides: Toward S N 2-Selective Transition-Metal-Free Formal Hydrocarbonation

Organic Letters 2026

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Authors: Raju Teegala, Purna C. R. Bhavnari, Kadiyala Sagar, Arun B. Ingle, Tapas R. Pradhan, Jin Kyoon Park
DOI: 10.1021/acs.orglett.5c05174
Cited by: 2
References: 34

Abstract

Two versatile synthetic strategies for β-H/F-enamide-tagged phosphoro(di)thioates from allenamides are disclosed, relying on electrophilic activation via β-H and F-iminium species. These developed straightforward protocols demonstrate broad applicability in complex molecular contexts with remarkable chemo- and regioselectivity. The synthesized allylphosphorothioates (APTs) act as potent electrophiles, enabling S N 2-selective allylic substitution with (hard)C-nucleophiles of all hybridizations to deliver hydrocarbonation products in seamless complement to transition-metal-driven strategies.

Fields of Study & Subjects

Sulfur-Based Synthesis Techniques Catalytic C–H Functionalization Methods Organophosphorus compounds synthesis

Publication details

Journal / source
Organic Letters
Publisher
American Chemical Society (ACS)
Volume
28
Issue
5
Pages
1678–1683
Publication date
26 January 2026
Language
EN