TY - JOUR
T1 - C−C Bond Formation of Benzyl Alcohols and Alkynes Using a Catalytic Amount of KO t Bu
T2 - Unusual Regioselectivity through a Radical Mechanism
AU - Kumar, Amit
AU - Janes, Trevor
AU - Chakraborty, Subrata
AU - Daw, Prosenjit
AU - von Wolff, Niklas
AU - Carmieli, Raanan
AU - Diskin-Posner, Yael
AU - Milstein, David
N1 - Funding Information:
D.M. holds the Israel Matz Professorial Chair of Organic Chemistry. A.K. is thankful to the Israel Planning and Budgeting Commission (PBC) for a fellowship. T.J. thanks the Azrieli Foundation for a postdoctoral fellowship. P.D. thanks the PBC and Koshland Foundation for the Senior Postdoctoral Fellowship. N.v.W. is supported by the Foreign Postdoctoral Fellowship Program of the Israel Academy of Sciences and Humanities. We are thankful to Prof. Ronny Neumann, Prof. Rafal Klajn and their research group members (Dr. Eynat Haviv from the Neumann group and Mr. Pankaj Maity and Dr. Saumen De from the Klajn group) for their help with the instrumentation facility.
PY - 2019/3/11
Y1 - 2019/3/11
N2 - 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.
AB - 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.
KW - alkynes
KW - benzyl alcohols
KW - potassium tert-butoxide
KW - radicals
KW - α-alkylated ketones
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U2 - 10.1002/anie.201812687
DO - 10.1002/anie.201812687
M3 - Article
C2 - 30605258
AN - SCOPUS:85061235271
VL - 58
SP - 3373
EP - 3377
JO - Angewandte Chemie - International Edition
JF - Angewandte Chemie - International Edition
SN - 1433-7851
IS - 11
ER -