Related Experiment Video
Updated: Aug 15, 2026

Synthesis of a Borylated Ibuprofen Derivative Through Suzuki Cross-Coupling and Alkene Boracarboxylation Reactions
Published on: November 30, 2022
Kumada coupling of aryl and vinyl tosylates under mild conditions
Michael E Limmert1, Amy H Roy, John F Hartwig
1Department of Chemistry, Yale University, P.O. Box 208107, New Haven, Connecticut 06520-8107, USA.
Abstract:
[Reaction: see text]. Aryl and alkenyl tosylates are easily prepared, inexpensive and, thus, attractive for transition-metal-catalyzed couplings, but their reactivity is low. We report examples of mild, palladium-catalyzed coupling of aryl, alkenyl, and alkyl Grignard reagents with aryl and alkenyl tosylates. The resulting biaryls, vinylarenes, and alkylarenes were isolated in good to excellent yield. These couplings were conducted with a nearly equimolar ratio of the two reactants, and many examples were conducted at room temperature.
Related Concept Videos
Vicinal Diols via Reductive Coupling of Aldehydes or Ketones: Pinacol Coupling Overview
Aryldiazonium Salts to Azo Dyes: Diazo Coupling
Alkenes via Reductive Coupling of Aldehydes or Ketones: McMurry Reaction
Dehydration of Aldols to Enones: Acid-Catalyzed Aldol Condensation
Aldol Condensation with β-Diesters: Knoevenagel Condensation
α-Hydroxy Ketones via Reductive Coupling of Esters: Acyloin Condensation Overview

