One-Pot Iridium Catalyzed C–H Borylation/Sonogashira Cross-Coupling: Access to Borylated Aryl Alkynes

Ghayoor A. Chotana; Jose R. Montero Bastidas; Susanne L. Miller; Milton R. Smith; Robert E. Maleczka

doi:10.3390/molecules25071754

Molecules (Apr 2020)

One-Pot Iridium Catalyzed C–H Borylation/Sonogashira Cross-Coupling: Access to Borylated Aryl Alkynes

Ghayoor A. Chotana,
Jose R. Montero Bastidas,
Susanne L. Miller,
Milton R. Smith,
Robert E. Maleczka

Affiliations

Ghayoor A. Chotana: Department of Chemistry, Michigan State University, East Lansing, MI 48824-1322, USA
Jose R. Montero Bastidas: Department of Chemistry, Michigan State University, East Lansing, MI 48824-1322, USA
Susanne L. Miller: BoroPharm Inc., 39555 Orchard Hill Place, Suite 600, Novi, MI 48375, USA
Milton R. Smith: Department of Chemistry, Michigan State University, East Lansing, MI 48824-1322, USA
Robert E. Maleczka: Department of Chemistry, Michigan State University, East Lansing, MI 48824-1322, USA

DOI: https://doi.org/10.3390/molecules25071754
Journal volume & issue: Vol. 25, no. 7
p. 1754

Abstract

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Borylated aryl alkynes have been synthesized via one-pot iridium catalyzed C–H borylation (CHB)/Sonogashira cross-coupling of aryl bromides. Direct borylation of aryl alkynes encountered problems related to the reactivity of the alkyne under CHB conditions. However, tolerance of aryl bromides to CHB made possible a subsequent Sonogashira cross-coupling to access the desired borylated aryl alkynes.

Published in Molecules

ISSN: 1420-3049 (Online)
Publisher: MDPI AG
Country of publisher: Switzerland
LCC subjects: Science: Chemistry: Organic chemistry
Website: http://www.mdpi.com/journal/molecules

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