Photocatalytic decarboxylative selenocyanation of 2-aryloxy and 2-aryl carboxylic acids with N-selenocyanatophthalimide

Yong Gao; Ruirui Hua; Hongquan Yin; Fu Xue Chen

doi:10.1039/d3qo00347g

Photocatalytic decarboxylative selenocyanation of 2-aryloxy and 2-aryl carboxylic acids with N-selenocyanatophthalimide

Yong Gao, Ruirui Hua, 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

4 Citations (Scopus)

Abstract

A visible-light-induced decarboxylative selenocyanation reaction of aliphatic carboxylic acids for the formation of C(sp³)-SeCN bonds has been developed. The electrophilic N-selenocyanatophthalimide and a pyrylium salt were applied as a SeCN radical precursor and an organic photocatalyst, respectively. The transformation could proceed smoothly without transition metals, oxidants and additional bases, affording the corresponding alkyl selenocyanates in moderate to good yields. This method is characterized by its simplicity, wide substrate scope and mild conditions.

Original language	English
Pages (from-to)	2538-2543
Number of pages	6
Journal	Organic Chemistry Frontiers
Volume	10
Issue number	10
DOIs	https://doi.org/10.1039/d3qo00347g
Publication status	Published - 24 Apr 2023

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title = "Photocatalytic decarboxylative selenocyanation of 2-aryloxy and 2-aryl carboxylic acids with N-selenocyanatophthalimide",

abstract = "A visible-light-induced decarboxylative selenocyanation reaction of aliphatic carboxylic acids for the formation of C(sp3)-SeCN bonds has been developed. The electrophilic N-selenocyanatophthalimide and a pyrylium salt were applied as a SeCN radical precursor and an organic photocatalyst, respectively. The transformation could proceed smoothly without transition metals, oxidants and additional bases, affording the corresponding alkyl selenocyanates in moderate to good yields. This method is characterized by its simplicity, wide substrate scope and mild conditions.",

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

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T1 - Photocatalytic decarboxylative selenocyanation of 2-aryloxy and 2-aryl carboxylic acids with N-selenocyanatophthalimide

AU - Gao, Yong

AU - Hua, Ruirui

AU - Yin, Hongquan

AU - Chen, Fu Xue

PY - 2023/4/24

Y1 - 2023/4/24

N2 - A visible-light-induced decarboxylative selenocyanation reaction of aliphatic carboxylic acids for the formation of C(sp3)-SeCN bonds has been developed. The electrophilic N-selenocyanatophthalimide and a pyrylium salt were applied as a SeCN radical precursor and an organic photocatalyst, respectively. The transformation could proceed smoothly without transition metals, oxidants and additional bases, affording the corresponding alkyl selenocyanates in moderate to good yields. This method is characterized by its simplicity, wide substrate scope and mild conditions.

AB - A visible-light-induced decarboxylative selenocyanation reaction of aliphatic carboxylic acids for the formation of C(sp3)-SeCN bonds has been developed. The electrophilic N-selenocyanatophthalimide and a pyrylium salt were applied as a SeCN radical precursor and an organic photocatalyst, respectively. The transformation could proceed smoothly without transition metals, oxidants and additional bases, affording the corresponding alkyl selenocyanates in moderate to good yields. This method is characterized by its simplicity, wide substrate scope and mild conditions.

UR - http://www.scopus.com/inward/record.url?scp=85153798493&partnerID=8YFLogxK

U2 - 10.1039/d3qo00347g

DO - 10.1039/d3qo00347g

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SN - 2052-4110

VL - 10

SP - 2538

EP - 2543

JO - Organic Chemistry Frontiers

JF - Organic Chemistry Frontiers

IS - 10

ER -

Photocatalytic decarboxylative selenocyanation of 2-aryloxy and 2-aryl carboxylic acids with N-selenocyanatophthalimide

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