Mechanochemical Synthesis of Ketones via Chemoselective Suzuki-Miyaura Cross-Coupling of Acyl Chlorides

Jin Zhang; Pei Zhang; Yangmin Ma; Michal Szostak

doi:10.1021/acs.orglett.2c00519

Mechanochemical Synthesis of Ketones via Chemoselective Suzuki-Miyaura Cross-Coupling of Acyl Chlorides

Jin Zhang, Pei Zhang, Yangmin Ma, Michal Szostak

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

16 Scopus citations

Abstract

The direct synthesis of ketones via acyl Suzuki-Miyaura cross-coupling of widely available acyl chlorides is a central transformation in organic synthesis. Herein, we report the first mechanochemical solvent-free method for highly chemoselective synthesis of ketones from acyl chlorides and boronic acids. This acylation reaction is conducted in the solid state, in the absence of potentially harmful solvents, for a short reaction time and shows excellent selectivity for C(acyl)-Cl bond cleavage.

Original language	English (US)
Pages (from-to)	2338-2343
Number of pages	6
Journal	Organic letters
Volume	24
Issue number	12
DOIs	https://doi.org/10.1021/acs.orglett.2c00519
State	Published - Apr 1 2022
Externally published	Yes

All Science Journal Classification (ASJC) codes

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/acs.orglett.2c00519

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abstract = "The direct synthesis of ketones via acyl Suzuki-Miyaura cross-coupling of widely available acyl chlorides is a central transformation in organic synthesis. Herein, we report the first mechanochemical solvent-free method for highly chemoselective synthesis of ketones from acyl chlorides and boronic acids. This acylation reaction is conducted in the solid state, in the absence of potentially harmful solvents, for a short reaction time and shows excellent selectivity for C(acyl)-Cl bond cleavage.",

author = "Jin Zhang and Pei Zhang and Yangmin Ma and Michal Szostak",

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language = "English (US)",

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T1 - Mechanochemical Synthesis of Ketones via Chemoselective Suzuki-Miyaura Cross-Coupling of Acyl Chlorides

AU - Zhang, Jin

AU - Zhang, Pei

AU - Ma, Yangmin

AU - Szostak, Michal

PY - 2022/4/1

Y1 - 2022/4/1

N2 - The direct synthesis of ketones via acyl Suzuki-Miyaura cross-coupling of widely available acyl chlorides is a central transformation in organic synthesis. Herein, we report the first mechanochemical solvent-free method for highly chemoselective synthesis of ketones from acyl chlorides and boronic acids. This acylation reaction is conducted in the solid state, in the absence of potentially harmful solvents, for a short reaction time and shows excellent selectivity for C(acyl)-Cl bond cleavage.

AB - The direct synthesis of ketones via acyl Suzuki-Miyaura cross-coupling of widely available acyl chlorides is a central transformation in organic synthesis. Herein, we report the first mechanochemical solvent-free method for highly chemoselective synthesis of ketones from acyl chlorides and boronic acids. This acylation reaction is conducted in the solid state, in the absence of potentially harmful solvents, for a short reaction time and shows excellent selectivity for C(acyl)-Cl bond cleavage.

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JO - Organic letters

JF - Organic letters

IS - 12

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Mechanochemical Synthesis of Ketones via Chemoselective Suzuki-Miyaura Cross-Coupling of Acyl Chlorides

Abstract

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