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 journal › Article

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
JournalAngewandte Chemie - International Edition
DOIs
Publication statusPublished - Jan 1 2019

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Benzyl Alcohols
Regioselectivity
Alkynes
Ketones
Alcohols
Atoms
Hot Temperature

Keywords

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

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

Cite this

C−C Bond Formation of Benzyl Alcohols and Alkynes Using a Catalytic Amount of KO t Bu : Unusual Regioselectivity through a Radical Mechanism. / Kumar, Amit; Janes, Trevor; Chakraborty, Subrata; Daw, Prosenjit; von Wolff, Niklas; Carmieli, Raanan; Diskin-Posner, Yael; Milstein, David.

In: Angewandte Chemie - International Edition, 01.01.2019.

Research output: Contribution to journal › Article

Kumar, A, Janes, T, Chakraborty, S, Daw, P, von Wolff, N, Carmieli, R, Diskin-Posner, Y & Milstein, D 2019, 'C−C Bond Formation of Benzyl Alcohols and Alkynes Using a Catalytic Amount of KO t Bu: Unusual Regioselectivity through a Radical Mechanism', Angewandte Chemie - International Edition. https://doi.org/10.1002/anie.201812687
Kumar A, Janes T, Chakraborty S, Daw P, von Wolff N, Carmieli R et al. C−C Bond Formation of Benzyl Alcohols and Alkynes Using a Catalytic Amount of KO t Bu: Unusual Regioselectivity through a Radical Mechanism. Angewandte Chemie - International Edition. 2019 Jan 1. https://doi.org/10.1002/anie.201812687
Kumar, Amit ; Janes, Trevor ; Chakraborty, Subrata ; Daw, Prosenjit ; von Wolff, Niklas ; Carmieli, Raanan ; Diskin-Posner, Yael ; Milstein, David. / C−C Bond Formation of Benzyl Alcohols and Alkynes Using a Catalytic Amount of KO t Bu : Unusual Regioselectivity through a Radical Mechanism. In: Angewandte Chemie - International Edition. 2019.
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