Metal-, Photocatalyst-, and Light-Free, Late-Stage C–H Alkylation of Heteroarenes and 1,4-Quinones Using Carboxylic Acids

Daniel R. Sutherland; Marcos Veguillas; Conor L. Oates; Ai-lan Lee

doi:10.1021/acs.orglett.8b02988

Metal-, Photocatalyst-, and Light-Free, Late-Stage C–H Alkylation of Heteroarenes and 1,4-Quinones Using Carboxylic Acids

Daniel R. Sutherland, Marcos Veguillas, Conor L. Oates, Ai-lan Lee

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

83 Citations (Scopus)

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Abstract

Contrary to the accepted convention, this work shows that Minisci-type C–H alkylation does not require any metal, photocatalyst, light, or prefunctionalization of the readily available and inexpensive carboxylic acids to proceed well under mild conditions. These mild conditions can be utilized for late-stage alkylations of complex molecules, including pharmaceutical compounds and light-sensitive compounds which degrade under photocatalytic conditions.

Original language	English
Pages (from-to)	6863-6867
Number of pages	5
Journal	Organic Letters
Volume	20
Issue number	21
Early online date	24 Oct 2018
DOIs	https://doi.org/10.1021/acs.orglett.8b02988
Publication status	Published - 2 Nov 2018

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This document is the Accepted Manuscript version of a Published Work that appeared in final form in Organic Letters, copyright © American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see https://pubs.acs.org/doi/10.1021/acs.orglett.8b02988
Accepted author manuscript, 1.02 MBLicence: Copyright Publisher

Ai-Lan Lee
- a.leehw.acuk
- School of Engineering & Physical Sciences - Associate Professor
- School of Engineering & Physical Sciences, Institute of Chemical Sciences - Associate Professor
Person: Academic (Research & Teaching)

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title = "Metal-, Photocatalyst-, and Light-Free, Late-Stage C–H Alkylation of Heteroarenes and 1,4-Quinones Using Carboxylic Acids",

abstract = "Contrary to the accepted convention, this work shows that Minisci-type C–H alkylation does not require any metal, photocatalyst, light, or prefunctionalization of the readily available and inexpensive carboxylic acids to proceed well under mild conditions. These mild conditions can be utilized for late-stage alkylations of complex molecules, including pharmaceutical compounds and light-sensitive compounds which degrade under photocatalytic conditions.",

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AU - Sutherland, Daniel R.

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AU - Oates, Conor L.

AU - Lee, Ai-lan

PY - 2018/11/2

Y1 - 2018/11/2

N2 - Contrary to the accepted convention, this work shows that Minisci-type C–H alkylation does not require any metal, photocatalyst, light, or prefunctionalization of the readily available and inexpensive carboxylic acids to proceed well under mild conditions. These mild conditions can be utilized for late-stage alkylations of complex molecules, including pharmaceutical compounds and light-sensitive compounds which degrade under photocatalytic conditions.

AB - Contrary to the accepted convention, this work shows that Minisci-type C–H alkylation does not require any metal, photocatalyst, light, or prefunctionalization of the readily available and inexpensive carboxylic acids to proceed well under mild conditions. These mild conditions can be utilized for late-stage alkylations of complex molecules, including pharmaceutical compounds and light-sensitive compounds which degrade under photocatalytic conditions.

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JO - Organic Letters

JF - Organic Letters

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ER -

Metal-, Photocatalyst-, and Light-Free, Late-Stage C–H Alkylation of Heteroarenes and 1,4-Quinones Using Carboxylic Acids

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