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One-Pot Conversion of Aldehydes and Aryl Halides to Disubstituted Alkynes via Tandem Seyferth–Gilbert Homologation/Copper-Free Sonogashira Coupling

Author:
Sapegin, Alexander, Krasavin, Mikhail
Source:
Journal of organic chemistry 2019 v.84 no.13 pp. 8788-8795
ISSN:
1520-6904
Subject:
acetylene, aldehydes, catalysts, chemical reactions, chemical structure, copper, organic chemistry, organic halogen compounds, palladium
Abstract:
A practically convenient protocol has been developed to convert a mixture of an aldehyde, aryl halide, and the Bestmann–Ohira reagent into disubstituted acetylene via a successive addition of base (Cs₂CO₃) and a Pd(II) catalyst, allowing sufficient time after addition of each of these reagents for the tandem processes (Seyferth–Gilbert homologation and Sonogashira coupling) to occur. Notably, for the latter reaction, no copper catalyst was required.
Agid:
6496749