Visible-Light-Mediated Synthesis of N -Acyl- N,O -hemiacetals from Terminal Alkynes: Access to N,N- , N,S- , and N,O- Acetals.

Autor: Ganie MA; Academy of Scientific and Innovative Research (AcSIR), Ghaziabad-201002, India.; Natural Product & Medicinal Chemistry, CSIR-Indian Institute of Integrative Medicine, Jammu-180001, India., Fayaz F; Academy of Scientific and Innovative Research (AcSIR), Ghaziabad-201002, India.; Natural Product & Medicinal Chemistry, CSIR-Indian Institute of Integrative Medicine, Jammu-180001, India., Bhat MU; Academy of Scientific and Innovative Research (AcSIR), Ghaziabad-201002, India.; Natural Product & Medicinal Chemistry, CSIR-Indian Institute of Integrative Medicine, Jammu-180001, India., Rizvi MA; Department of Chemistry, University of Kashmir, Srinagar-190006, India., Raheem S; Department of Chemistry, University of Kashmir, Srinagar-190006, India., Shah BA; Academy of Scientific and Innovative Research (AcSIR), Ghaziabad-201002, India.; Natural Product & Medicinal Chemistry, CSIR-Indian Institute of Integrative Medicine, Jammu-180001, India.
Jazyk: angličtina
Zdroj: Organic letters [Org Lett] 2023 Nov 24; Vol. 25 (46), pp. 8234-8239. Date of Electronic Publication: 2023 Nov 14.
DOI: 10.1021/acs.orglett.3c03263
Abstrakt: A mild electron donor-acceptor complex-mediated approach for the synthesis of N -acyl- N,O -hemiacetals has been reported. The key feature of this protocol is that it allows for direct access to electrophilic N -acylimines at room temperature without prefunctionalization of the hydroxyl group. The in situ generated N -acylimine can react with different nucleophiles, viz., alcohols, thiols, and nitriles, to afford a diverse range of scaffolds such as N,O -, N,S -, and N,N -acetals.
Databáze: MEDLINE