Electrochemical Benzylic C(sp3)−H Acyloxylation

Alastair J J Lennox; Alex Atkins; Bert C Rowett; David M Heard; Joseph A Tate

doi:10.1021/acs.orglett.2c01930

Electrochemical Benzylic C(sp3)−H Acyloxylation

Alastair J J Lennox, Alex Atkins, Bert C Rowett, David M Heard, Joseph A Tate

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Abstract

The development of sustainable C(sp3)−H function- alization methods is of great interest to the pharmaceutical and agrochemical industries. Anodic oxidation is an efficient means of producing benzylic cations that can undergo subsequent in situ nucleophilic attack to afford functionalized benzylic products. Herein, we demonstrate the suitability of carboxylic acids as nucleophiles to yield benzylic esters. This method employs a series of secondary benzylic substrates and functionalized carboxylic acids and is demonstrated on a gram scale in flow

Original language	English
Pages (from-to)	5105-5108
Number of pages	4
Journal	Organic Letters
Volume	24
Issue number	28
DOIs	https://doi.org/10.1021/acs.orglett.2c01930
Publication status	Published - 13 Jul 2022

Bibliographical note

Funding Information:
The authors thank the Royal Society (University Research Fellowship and Enhancement Awards to A.J.J.L.), EPSRC (EP/T001631/1, EP/L016443/1, and EP/S018050/1), and Syngenta for funding.

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© 2022 The Authors. Published by American Chemical Society.

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title = "Electrochemical Benzylic C(sp3)−H Acyloxylation",

abstract = "The development of sustainable C(sp3)−H function- alization methods is of great interest to the pharmaceutical and agrochemical industries. Anodic oxidation is an efficient means of producing benzylic cations that can undergo subsequent in situ nucleophilic attack to afford functionalized benzylic products. Herein, we demonstrate the suitability of carboxylic acids as nucleophiles to yield benzylic esters. This method employs a series of secondary benzylic substrates and functionalized carboxylic acids and is demonstrated on a gram scale in flow",

author = "Lennox, {Alastair J J} and Alex Atkins and Rowett, {Bert C} and Heard, {David M} and Tate, {Joseph A}",

note = "Funding Information: The authors thank the Royal Society (University Research Fellowship and Enhancement Awards to A.J.J.L.), EPSRC (EP/T001631/1, EP/L016443/1, and EP/S018050/1), and Syngenta for funding. Publisher Copyright: {\textcopyright} 2022 The Authors. Published by American Chemical Society.",

year = "2022",

month = jul,

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doi = "10.1021/acs.orglett.2c01930",

language = "English",

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T1 - Electrochemical Benzylic C(sp3)−H Acyloxylation

AU - Lennox, Alastair J J

AU - Atkins, Alex

AU - Rowett, Bert C

AU - Heard, David M

AU - Tate, Joseph A

N1 - Funding Information: The authors thank the Royal Society (University Research Fellowship and Enhancement Awards to A.J.J.L.), EPSRC (EP/T001631/1, EP/L016443/1, and EP/S018050/1), and Syngenta for funding. Publisher Copyright: © 2022 The Authors. Published by American Chemical Society.

PY - 2022/7/13

Y1 - 2022/7/13

N2 - The development of sustainable C(sp3)−H function- alization methods is of great interest to the pharmaceutical and agrochemical industries. Anodic oxidation is an efficient means of producing benzylic cations that can undergo subsequent in situ nucleophilic attack to afford functionalized benzylic products. Herein, we demonstrate the suitability of carboxylic acids as nucleophiles to yield benzylic esters. This method employs a series of secondary benzylic substrates and functionalized carboxylic acids and is demonstrated on a gram scale in flow

AB - The development of sustainable C(sp3)−H function- alization methods is of great interest to the pharmaceutical and agrochemical industries. Anodic oxidation is an efficient means of producing benzylic cations that can undergo subsequent in situ nucleophilic attack to afford functionalized benzylic products. Herein, we demonstrate the suitability of carboxylic acids as nucleophiles to yield benzylic esters. This method employs a series of secondary benzylic substrates and functionalized carboxylic acids and is demonstrated on a gram scale in flow

U2 - 10.1021/acs.orglett.2c01930

DO - 10.1021/acs.orglett.2c01930

M3 - Article (Academic Journal)

C2 - 35829756

SN - 1523-7060

VL - 24

SP - 5105

EP - 5108

JO - Organic Letters

JF - Organic Letters

IS - 28

ER -

Electrochemical Benzylic C(sp3)−H Acyloxylation

Abstract

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