C−C Bond Formation of Benzyl Alcohols and Alkynes Using a Catalytic Amount of KO t Bu: Unusual Regioselectivity through a Radical Mechanism

Amit Kumar, Trevor Janes, Subrata Chakraborty, Prosenjit Daw, Niklas von Wolff, Raanan Carmieli, Yael Diskin-Posner, David Milstein

Research output: Contribution to journalArticle

7 Citations (Scopus)

Abstract

We report a C−C bond-forming reaction between benzyl alcohols and alkynes in the presence of a catalytic amount of KO t Bu to form α-alkylated ketones in which the C=O group is located on the side derived from the alcohol. The reaction proceeds under thermal conditions (125 °C) and produces no waste, making the reaction highly atom efficient, environmentally benign, and sustainable. Based on our mechanistic investigations, we propose that the reaction proceeds through radical pathways.

Original languageEnglish
Pages (from-to)3373-3377
Number of pages5
JournalAngewandte Chemie - International Edition
Volume58
Issue number11
DOIs
Publication statusPublished - Mar 11 2019

Keywords

  • alkynes
  • benzyl alcohols
  • potassium tert-butoxide
  • radicals
  • α-alkylated ketones

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

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