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

doi:10.1002/anie.201812687

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

Weizmann Institute of Science, Israel

Research output: Contribution to journal › Article

8 Citations (Scopus)

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
Pages (from-to)	3373-3377
Number of pages	5
Journal	Angewandte Chemie - International Edition
Volume	58
Issue number	11
DOIs	https://doi.org/10.1002/anie.201812687
Publication status	Published - Mar 11 2019

Keywords

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

ASJC Scopus subject areas

Catalysis
Chemistry(all)

Access to Document

10.1002/anie.201812687

Fingerprint Dive into the research topics of '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'. Together they form a unique fingerprint.

Cite this

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, 58(11), 3373-3377. https://doi.org/10.1002/anie.201812687

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, Vol. 58, No. 11, 11.03.2019, p. 3373-3377.

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, vol. 58, no. 11, pp. 3373-3377. 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 Mar 11;58(11):3373-3377. 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 ; Vol. 58, No. 11. pp. 3373-3377.

@article{34b760315f5249269e03180b00a3017e,

title = "C−C Bond Formation of Benzyl Alcohols and Alkynes Using a Catalytic Amount of KO t Bu: Unusual Regioselectivity through a Radical Mechanism",

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. ",

keywords = "alkynes, benzyl alcohols, potassium tert-butoxide, radicals, α-alkylated ketones",

author = "Amit Kumar and Trevor Janes and Subrata Chakraborty and Prosenjit Daw and {von Wolff}, Niklas and Raanan Carmieli and Yael Diskin-Posner and David Milstein",

year = "2019",

month = mar,

day = "11",

doi = "10.1002/anie.201812687",

language = "English",

volume = "58",

pages = "3373--3377",

journal = "Angewandte Chemie - International Edition",

issn = "1433-7851",

publisher = "John Wiley and Sons Ltd",

number = "11",

}

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 - 2019/3/11

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

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

VL - 58

SP - 3373

EP - 3377

JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

SN - 1433-7851

IS - 11

ER -