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- Title
C−C Bond Formation of Benzyl Alcohols and Alkynes Using a Catalytic Amount of KO<sup>t</sup>Bu: Unusual Regioselectivity through a Radical Mechanism.
- Authors
Kumar, Amit; Janes, Trevor; Chakraborty, Subrata; Daw, Prosenjit; von Wolff, Niklas; Carmieli, Raanan; Diskin‐Posner, Yael; Milstein, David
- 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.
- Subjects
CARBON-carbon bonds; BENZYL alcohol; ALKYNES; CATALYSIS; REGIOSELECTIVITY (Chemistry); RADICALS (Chemistry); POTASSIUM compounds
- Publication
Angewandte Chemie, 2019, Vol 131, Issue 11, p3411
- ISSN
0044-8249
- Publication type
Article
- DOI
10.1002/ange.201812687