Photoredox-Mediated Minisci Alkylation of N-Heteroarenes using Carboxylic Acids and Hypervalent Iodine

Junhua Wang; Guo Xing Li; Gang He; Gong Chen

doi:10.1002/ajoc.201800197

Photoredox-Mediated Minisci Alkylation of N-Heteroarenes using Carboxylic Acids and Hypervalent Iodine

Junhua Wang, Guo Xing Li, Gang He, Gong Chen

Chemistry

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

54 Scopus citations

Abstract

A new protocol of photoredox-mediated Minisci alkylation of N-heteroarenes with aliphatic carboxylic acids has been developed. Using Ru(bpy)₃Cl₂ as photocatalyst and acetoxybenziodoxole (BI–OAc) as oxidant, a variety of primary, secondary and tertiary alkyl groups can be efficiently incorporated into various electron-deficient N-heteroarenes. This protocol demonstrated excellent substrate scope and good functional group tolerance and can be applied to late-stage functionalization of complex molecules.

Original language	English (US)
Pages (from-to)	1307-1310
Number of pages	4
Journal	Asian Journal of Organic Chemistry
Volume	7
Issue number	7
DOIs	https://doi.org/10.1002/ajoc.201800197
State	Published - Jul 2018

All Science Journal Classification (ASJC) codes

Organic Chemistry

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10.1002/ajoc.201800197

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title = "Photoredox-Mediated Minisci Alkylation of N-Heteroarenes using Carboxylic Acids and Hypervalent Iodine",

abstract = "A new protocol of photoredox-mediated Minisci alkylation of N-heteroarenes with aliphatic carboxylic acids has been developed. Using Ru(bpy)3Cl2 as photocatalyst and acetoxybenziodoxole (BI–OAc) as oxidant, a variety of primary, secondary and tertiary alkyl groups can be efficiently incorporated into various electron-deficient N-heteroarenes. This protocol demonstrated excellent substrate scope and good functional group tolerance and can be applied to late-stage functionalization of complex molecules.",

author = "Junhua Wang and Li, {Guo Xing} and Gang He and Gong Chen",

note = "Funding Information: We gratefully thank the State Key Laboratory of Elemento-Organic Chemistry at Nankai University, NSFC 21421062, 21672105 and China Postdoctoral Science Foundation (2016M591383) for financial support of this work. Publisher Copyright: {\textcopyright} 2018 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim",

year = "2018",

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AU - Wang, Junhua

AU - Li, Guo Xing

AU - He, Gang

AU - Chen, Gong

N1 - Funding Information: We gratefully thank the State Key Laboratory of Elemento-Organic Chemistry at Nankai University, NSFC 21421062, 21672105 and China Postdoctoral Science Foundation (2016M591383) for financial support of this work. Publisher Copyright: © 2018 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim

PY - 2018/7

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N2 - A new protocol of photoredox-mediated Minisci alkylation of N-heteroarenes with aliphatic carboxylic acids has been developed. Using Ru(bpy)3Cl2 as photocatalyst and acetoxybenziodoxole (BI–OAc) as oxidant, a variety of primary, secondary and tertiary alkyl groups can be efficiently incorporated into various electron-deficient N-heteroarenes. This protocol demonstrated excellent substrate scope and good functional group tolerance and can be applied to late-stage functionalization of complex molecules.

AB - A new protocol of photoredox-mediated Minisci alkylation of N-heteroarenes with aliphatic carboxylic acids has been developed. Using Ru(bpy)3Cl2 as photocatalyst and acetoxybenziodoxole (BI–OAc) as oxidant, a variety of primary, secondary and tertiary alkyl groups can be efficiently incorporated into various electron-deficient N-heteroarenes. This protocol demonstrated excellent substrate scope and good functional group tolerance and can be applied to late-stage functionalization of complex molecules.

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Photoredox-Mediated Minisci Alkylation of N-Heteroarenes using Carboxylic Acids and Hypervalent Iodine

Abstract

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