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

Alexander Sapegin, Mikhail Krasavin*

*Saint Petersburg State University, Saint Petersburg 199034, Russia, Email: m.krasavinspbu.ru

A. Sapegin, M. Krasavin, J. Org. Chem., 2019, 84, 8788-8795.

DOI: 10.1021/acs.joc.9b01367

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Abstract

A mixture of an aldehyde, aryl halide, and the Bestmann-Ohira reagent can be converted into disubstituted acetylene via a successive addition of Cs₂CO₃ and a Pd(II) catalyst, allowing sufficient time for the Seyferth-Gilbert homologation and Sonogashira coupling to occur. Notably, for the latter reaction, no copper catalyst was required.

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Key Words

Seyferth-Gilbert Homologation, Sonogashira Coupling

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ID: J42-Y2019