Metal-Free Synthesis of N-(Pyridine-2-yl)amides from Ketones via Selective Oxidative Cleavage of C(O)-C(Alkyl) Bond in Water

Yanpeng Liu; Honghao Sun; Zhangjian Huang; Cong Ma; Aijun Lin; Hequan Yao; Jinyi Xu; Shengtao Xu

doi:10.1021/acs.joc.8b01956

Metal-Free Synthesis of N-(Pyridine-2-yl)amides from Ketones via Selective Oxidative Cleavage of C(O)-C(Alkyl) Bond in Water

Yanpeng Liu, Honghao Sun, Zhangjian Huang, Cong Ma, Aijun Lin, Hequan Yao, Jinyi Xu, Shengtao Xu

Research output: Journal article publication › Journal article › Academic research › peer-review

23 Citations (Scopus)

Abstract

The TBHP/TBAI-mediated synthesis of N-(pyridine-2-yl)amides in water from ketones and 2-aminopyridine via direct oxidative C-C bond cleavage has been developed. A series of ketones, including more challenging inactive aromatic ketones substituted with diverse long-chain alkyl groups, were selectively converted to N-(pyridine-2-yl)amides. Furthermore, the protocol can be applied to aryl alkyl carbinols to afford the corresponding amides in moderate to good yields.

Original language	English
Pages (from-to)	14307-14313
Number of pages	7
Journal	Journal of Organic Chemistry
Volume	83
Issue number	23
DOIs	https://doi.org/10.1021/acs.joc.8b01956
Publication status	Published - 7 Dec 2018

ASJC Scopus subject areas

Organic Chemistry

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10.1021/acs.joc.8b01956

http://hdl.handle.net/10397/101547

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abstract = "The TBHP/TBAI-mediated synthesis of N-(pyridine-2-yl)amides in water from ketones and 2-aminopyridine via direct oxidative C-C bond cleavage has been developed. A series of ketones, including more challenging inactive aromatic ketones substituted with diverse long-chain alkyl groups, were selectively converted to N-(pyridine-2-yl)amides. Furthermore, the protocol can be applied to aryl alkyl carbinols to afford the corresponding amides in moderate to good yields.",

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AU - Liu, Yanpeng

AU - Sun, Honghao

AU - Huang, Zhangjian

AU - Ma, Cong

AU - Lin, Aijun

AU - Yao, Hequan

AU - Xu, Jinyi

AU - Xu, Shengtao

PY - 2018/12/7

Y1 - 2018/12/7

N2 - The TBHP/TBAI-mediated synthesis of N-(pyridine-2-yl)amides in water from ketones and 2-aminopyridine via direct oxidative C-C bond cleavage has been developed. A series of ketones, including more challenging inactive aromatic ketones substituted with diverse long-chain alkyl groups, were selectively converted to N-(pyridine-2-yl)amides. Furthermore, the protocol can be applied to aryl alkyl carbinols to afford the corresponding amides in moderate to good yields.

AB - The TBHP/TBAI-mediated synthesis of N-(pyridine-2-yl)amides in water from ketones and 2-aminopyridine via direct oxidative C-C bond cleavage has been developed. A series of ketones, including more challenging inactive aromatic ketones substituted with diverse long-chain alkyl groups, were selectively converted to N-(pyridine-2-yl)amides. Furthermore, the protocol can be applied to aryl alkyl carbinols to afford the corresponding amides in moderate to good yields.

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Metal-Free Synthesis of N-(Pyridine-2-yl)amides from Ketones via Selective Oxidative Cleavage of C(O)-C(Alkyl) Bond in Water

Abstract

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