Photoinduced remote heteroaryl migration accompanied by cyanoalkylacylation in continuous flow

Xiu Duan; Qi Sun; Xin Yuan; Long Zhou Qin; Xin Peng Zhang; Jie Liu; Meng Yu Wu; Shan Shan Zhu; Can Liang Ma; Jiang Kai Qiu; Kai Guo

doi:10.1039/d1gc03060d

Photoinduced remote heteroaryl migration accompanied by cyanoalkylacylation in continuous flow

Xiu Duan, Qi Sun, Xin Yuan, Long Zhou Qin, Xin Peng Zhang, Jie Liu, Meng Yu Wu, Shan Shan Zhu, Can Liang Ma, Jiang Kai Qiu, Kai Guo

COLLEGE OF BIOTECHNOLOGY AND PHARMACEUTICAL ENGINEERING

Nanjing Tech University

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

16 Scopus citations

Abstract

A photoinduced 1,4-heteroaryl migration from a carbon center to a nitrogen center accompanied by a cyanoalkylacylation of heterocyclic-substituted azidyl homoallylic alcohols and cycloketone oxime esters has been described. This simple and powerful protocol merged the dual C-C bond cleavage with C-N bond formation, providing an efficient and environmentally safe approach to a variety of synthetically useful cyanoalkyl-containing β-enamino ketones with outstanding selectivity and commendable functional group compatibility. Moreover, the application of microflow technique enhanced these reactions compared with the equivalent batch reaction, significantly reducing the reaction times to 5-9.3 min and broadening the substrate scope to more than 35 successful substrates.

Original language	English
Pages (from-to)	8916-8921
Number of pages	6
Journal	Green Chemistry
Volume	23
Issue number	22
DOIs	https://doi.org/10.1039/d1gc03060d
State	Published - 21 Nov 2021

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title = "Photoinduced remote heteroaryl migration accompanied by cyanoalkylacylation in continuous flow",

abstract = "A photoinduced 1,4-heteroaryl migration from a carbon center to a nitrogen center accompanied by a cyanoalkylacylation of heterocyclic-substituted azidyl homoallylic alcohols and cycloketone oxime esters has been described. This simple and powerful protocol merged the dual C-C bond cleavage with C-N bond formation, providing an efficient and environmentally safe approach to a variety of synthetically useful cyanoalkyl-containing β-enamino ketones with outstanding selectivity and commendable functional group compatibility. Moreover, the application of microflow technique enhanced these reactions compared with the equivalent batch reaction, significantly reducing the reaction times to 5-9.3 min and broadening the substrate scope to more than 35 successful substrates.",

author = "Xiu Duan and Qi Sun and Xin Yuan and Qin, {Long Zhou} and Zhang, {Xin Peng} and Jie Liu and Wu, {Meng Yu} and Zhu, {Shan Shan} and Ma, {Can Liang} and Qiu, {Jiang Kai} and Kai Guo",

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day = "21",

doi = "10.1039/d1gc03060d",

language = "英语",

volume = "23",

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T1 - Photoinduced remote heteroaryl migration accompanied by cyanoalkylacylation in continuous flow

AU - Duan, Xiu

AU - Sun, Qi

AU - Yuan, Xin

AU - Qin, Long Zhou

AU - Zhang, Xin Peng

AU - Liu, Jie

AU - Wu, Meng Yu

AU - Zhu, Shan Shan

AU - Ma, Can Liang

AU - Qiu, Jiang Kai

AU - Guo, Kai

PY - 2021/11/21

Y1 - 2021/11/21

N2 - A photoinduced 1,4-heteroaryl migration from a carbon center to a nitrogen center accompanied by a cyanoalkylacylation of heterocyclic-substituted azidyl homoallylic alcohols and cycloketone oxime esters has been described. This simple and powerful protocol merged the dual C-C bond cleavage with C-N bond formation, providing an efficient and environmentally safe approach to a variety of synthetically useful cyanoalkyl-containing β-enamino ketones with outstanding selectivity and commendable functional group compatibility. Moreover, the application of microflow technique enhanced these reactions compared with the equivalent batch reaction, significantly reducing the reaction times to 5-9.3 min and broadening the substrate scope to more than 35 successful substrates.

AB - A photoinduced 1,4-heteroaryl migration from a carbon center to a nitrogen center accompanied by a cyanoalkylacylation of heterocyclic-substituted azidyl homoallylic alcohols and cycloketone oxime esters has been described. This simple and powerful protocol merged the dual C-C bond cleavage with C-N bond formation, providing an efficient and environmentally safe approach to a variety of synthetically useful cyanoalkyl-containing β-enamino ketones with outstanding selectivity and commendable functional group compatibility. Moreover, the application of microflow technique enhanced these reactions compared with the equivalent batch reaction, significantly reducing the reaction times to 5-9.3 min and broadening the substrate scope to more than 35 successful substrates.

UR - http://www.scopus.com/inward/record.url?scp=85119622577&partnerID=8YFLogxK

U2 - 10.1039/d1gc03060d

DO - 10.1039/d1gc03060d

M3 - 文章

AN - SCOPUS:85119622577

SN - 1463-9262

VL - 23

SP - 8916

EP - 8921

JO - Green Chemistry

JF - Green Chemistry

IS - 22

ER -

Photoinduced remote heteroaryl migration accompanied by cyanoalkylacylation in continuous flow

Abstract

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