Electrophilic Thiocyanato Reagent Assisted Oxa-Michael/Thiocyanation of α,β-Unsaturated Ketones

Zhenda Fu; Yong Gao; Hongquan Yin; Fu Xue Chen

doi:10.1021/acs.joc.1c01993

Electrophilic Thiocyanato Reagent Assisted Oxa-Michael/Thiocyanation of α,β-Unsaturated Ketones

Zhenda Fu, Yong Gao, Hongquan Yin^*, Fu Xue Chen^*

^*Corresponding author for this work

School of Chemistry and Chemical Engineering

Beijing Institute of Technology

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

14 Citations (Scopus)

Abstract

A route for thiocyanation-functionalization of the electron-deficient C═C double bond was developed. Regioselective thiocyanation-etherification of α,β-unsaturated ketones was achieved. The desired products were obtained in moderate to high yields under mild conditions. It was suggested that the nucleophile was activated by the electrophilic thiocyanato reagent, and difunctionalization was achieved through a 1,4-addition/thiocyanation pathway.

Original language	English
Pages (from-to)	17418-17427
Number of pages	10
Journal	Journal of Organic Chemistry
Volume	86
Issue number	23
DOIs	https://doi.org/10.1021/acs.joc.1c01993
Publication status	Published - 3 Dec 2021

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title = "Electrophilic Thiocyanato Reagent Assisted Oxa-Michael/Thiocyanation of α,β-Unsaturated Ketones",

abstract = "A route for thiocyanation-functionalization of the electron-deficient C═C double bond was developed. Regioselective thiocyanation-etherification of α,β-unsaturated ketones was achieved. The desired products were obtained in moderate to high yields under mild conditions. It was suggested that the nucleophile was activated by the electrophilic thiocyanato reagent, and difunctionalization was achieved through a 1,4-addition/thiocyanation pathway.",

author = "Zhenda Fu and Yong Gao and Hongquan Yin and Chen, {Fu Xue}",

note = "Publisher Copyright: {\textcopyright} 2021 American Chemical Society",

year = "2021",

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day = "3",

doi = "10.1021/acs.joc.1c01993",

language = "English",

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journal = "Journal of Organic Chemistry",

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TY - JOUR

T1 - Electrophilic Thiocyanato Reagent Assisted Oxa-Michael/Thiocyanation of α,β-Unsaturated Ketones

AU - Fu, Zhenda

AU - Gao, Yong

AU - Yin, Hongquan

AU - Chen, Fu Xue

PY - 2021/12/3

Y1 - 2021/12/3

N2 - A route for thiocyanation-functionalization of the electron-deficient C═C double bond was developed. Regioselective thiocyanation-etherification of α,β-unsaturated ketones was achieved. The desired products were obtained in moderate to high yields under mild conditions. It was suggested that the nucleophile was activated by the electrophilic thiocyanato reagent, and difunctionalization was achieved through a 1,4-addition/thiocyanation pathway.

AB - A route for thiocyanation-functionalization of the electron-deficient C═C double bond was developed. Regioselective thiocyanation-etherification of α,β-unsaturated ketones was achieved. The desired products were obtained in moderate to high yields under mild conditions. It was suggested that the nucleophile was activated by the electrophilic thiocyanato reagent, and difunctionalization was achieved through a 1,4-addition/thiocyanation pathway.

UR - http://www.scopus.com/inward/record.url?scp=85120082988&partnerID=8YFLogxK

U2 - 10.1021/acs.joc.1c01993

DO - 10.1021/acs.joc.1c01993

M3 - Article

AN - SCOPUS:85120082988

SN - 0022-3263

VL - 86

SP - 17418

EP - 17427

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 23

ER -

Electrophilic Thiocyanato Reagent Assisted Oxa-Michael/Thiocyanation of α,β-Unsaturated Ketones

Abstract

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