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 language | English |
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Journal | Angewandte Chemie - International Edition |
DOIs | |
Publication status | Published - Jan 1 2019 |
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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
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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
PY - 2019/1/1
Y1 - 2019/1/1
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
UR - http://www.scopus.com/inward/record.url?scp=85061235271&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=85061235271&partnerID=8YFLogxK
U2 - 10.1002/anie.201812687
DO - 10.1002/anie.201812687
M3 - Article
C2 - 30605258
AN - SCOPUS:85061235271
JO - Angewandte Chemie - International Edition
JF - Angewandte Chemie - International Edition
SN - 1433-7851
ER -