Manganese-Catalyzed α-Alkylation of Ketones, Esters, and Amides Using Alcohols

Subrata Chakraborty; Prosenjit Daw; Yehoshoa Ben David; David Milstein

doi:10.1021/acscatal.8b03720

Manganese-Catalyzed α-Alkylation of Ketones, Esters, and Amides Using Alcohols

Subrata Chakraborty, Prosenjit Daw, Yehoshoa Ben David, David Milstein^*

^*Corresponding author for this work

Research output: Contribution to journal › Letter › peer-review

196 Citations (Scopus)

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Abstract

Herein we report the manganese-catalyzed C-C bond-forming reactions via α-alkylation of ketones, amides, and esters, using primary alcohols. β-Alkylation of secondary alcohols by primary alcohols to obtain α-alkylated ketones is also reported. The reactions are catalyzed by a ( ⁱPr-PNP)Mn(H)(CO) ₂ pincer complex under mild conditions in the presence of (catalytic) base liberating water (and H ₂ in the case of secondary alcohol alkylation) as the sole byproduct.

Original language	English
Pages (from-to)	10300-10305
Number of pages	6
Journal	ACS Catalysis
Volume	8
Issue number	11
DOIs	https://doi.org/10.1021/acscatal.8b03720
Publication status	Published - 2 Nov 2018

Funding

This research was supported by the European Research Council (ERC AdG 692775), and by the Israel Science Foundation. D.M. holds the Israel Matz Professorial Chair. P.D. thanks the Planning and Budgeting Committee (PBC) for a postdoctoral fellowship.

All Science Journal Classification (ASJC) codes

Catalysis
General Chemistry

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abstract = "Herein we report the manganese-catalyzed C-C bond-forming reactions via α-alkylation of ketones, amides, and esters, using primary alcohols. β-Alkylation of secondary alcohols by primary alcohols to obtain α-alkylated ketones is also reported. The reactions are catalyzed by a ( iPr-PNP)Mn(H)(CO) 2 pincer complex under mild conditions in the presence of (catalytic) base liberating water (and H 2 in the case of secondary alcohol alkylation) as the sole byproduct. ",

author = "Subrata Chakraborty and Prosenjit Daw and \{Ben David\}, Yehoshoa and David Milstein",

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T1 - Manganese-Catalyzed α-Alkylation of Ketones, Esters, and Amides Using Alcohols

AU - Chakraborty, Subrata

AU - Daw, Prosenjit

AU - Ben David, Yehoshoa

AU - Milstein, David

PY - 2018/11/2

Y1 - 2018/11/2

N2 - Herein we report the manganese-catalyzed C-C bond-forming reactions via α-alkylation of ketones, amides, and esters, using primary alcohols. β-Alkylation of secondary alcohols by primary alcohols to obtain α-alkylated ketones is also reported. The reactions are catalyzed by a ( iPr-PNP)Mn(H)(CO) 2 pincer complex under mild conditions in the presence of (catalytic) base liberating water (and H 2 in the case of secondary alcohol alkylation) as the sole byproduct.

AB - Herein we report the manganese-catalyzed C-C bond-forming reactions via α-alkylation of ketones, amides, and esters, using primary alcohols. β-Alkylation of secondary alcohols by primary alcohols to obtain α-alkylated ketones is also reported. The reactions are catalyzed by a ( iPr-PNP)Mn(H)(CO) 2 pincer complex under mild conditions in the presence of (catalytic) base liberating water (and H 2 in the case of secondary alcohol alkylation) as the sole byproduct.

U2 - 10.1021/acscatal.8b03720

DO - 10.1021/acscatal.8b03720

M3 - Letter

SN - 2155-5435

VL - 8

SP - 10300

EP - 10305

JO - ACS Catalysis

JF - ACS Catalysis

IS - 11

ER -

Manganese-Catalyzed α-Alkylation of Ketones, Esters, and Amides Using Alcohols

Abstract

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All Science Journal Classification (ASJC) codes

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