C−C bond formation of benzyl alcohols and alkynes using a catalytic amount of KOtBu: unusual regioselectivity through a radical mechanism

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

Research output: Contribution to journalArticlepeer-review

21 Citations (Scopus)

Abstract

We report a C−C bond‐forming reaction between benzyl alcohols and alkynes in the presence of a catalytic amount of KOtBu 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
JournalAngewandte Chemie International Edition
Volume58
Issue number11
Early online date7 Feb 2019
DOIs
Publication statusPublished - 4 Mar 2019

Keywords

  • Alkynes
  • Benzyl alcohols
  • Potassium tert-butoxide
  • Radicals
  • α-alkylated ketones

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