Organophotocatalytic Remote Thiocyanation Reaction via Ring-Opening Functionalization of Cycloalkanols

Ruirui Hua; Qing Wang; Hongquan Yin; Fu Xue Chen

doi:10.1002/chem.202400453

Organophotocatalytic Remote Thiocyanation Reaction via Ring-Opening Functionalization of Cycloalkanols

Ruirui Hua, Qing Wang, 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

Abstract

The remote C(sp³)-SCN bond formation via ring-opening functionalization of cycloalkanols with N-thiocyanatosaccharin as the precursor of SCN radicals and pyrylium salt as the organic photocatalyst under visible light has been developed. Thus, various terminal keto thiocyanates were prepared without transition metals and oxidants in moderate to good yields. The simplicity, wide substrate scope and mild conditions feature its synthetic application capability.

Original language	English
Article number	e202400453
Journal	Chemistry - A European Journal
Volume	30
Issue number	36
DOIs	https://doi.org/10.1002/chem.202400453
Publication status	Published - 25 Jun 2024

Keywords

alkyl thiocyanation
photocatalysis
ring-opening functionalization
synthetic methodology
terminal thiocyanatoketone

Access to Document

10.1002/chem.202400453

Cite this

@article{04553ab504644b6e9315117565d180d7,

title = "Organophotocatalytic Remote Thiocyanation Reaction via Ring-Opening Functionalization of Cycloalkanols",

abstract = "The remote C(sp3)-SCN bond formation via ring-opening functionalization of cycloalkanols with N-thiocyanatosaccharin as the precursor of SCN radicals and pyrylium salt as the organic photocatalyst under visible light has been developed. Thus, various terminal keto thiocyanates were prepared without transition metals and oxidants in moderate to good yields. The simplicity, wide substrate scope and mild conditions feature its synthetic application capability.",

keywords = "alkyl thiocyanation, photocatalysis, ring-opening functionalization, synthetic methodology, terminal thiocyanatoketone",

author = "Ruirui Hua and Qing Wang and Hongquan Yin and Chen, {Fu Xue}",

note = "Publisher Copyright: {\textcopyright} 2024 Wiley-VCH GmbH.",

year = "2024",

month = jun,

day = "25",

doi = "10.1002/chem.202400453",

language = "English",

volume = "30",

journal = "Chemistry - A European Journal",

issn = "0947-6539",

publisher = "Wiley-VCH Verlag",

number = "36",

}

TY - JOUR

T1 - Organophotocatalytic Remote Thiocyanation Reaction via Ring-Opening Functionalization of Cycloalkanols

AU - Hua, Ruirui

AU - Wang, Qing

AU - Yin, Hongquan

AU - Chen, Fu Xue

PY - 2024/6/25

Y1 - 2024/6/25

N2 - The remote C(sp3)-SCN bond formation via ring-opening functionalization of cycloalkanols with N-thiocyanatosaccharin as the precursor of SCN radicals and pyrylium salt as the organic photocatalyst under visible light has been developed. Thus, various terminal keto thiocyanates were prepared without transition metals and oxidants in moderate to good yields. The simplicity, wide substrate scope and mild conditions feature its synthetic application capability.

AB - The remote C(sp3)-SCN bond formation via ring-opening functionalization of cycloalkanols with N-thiocyanatosaccharin as the precursor of SCN radicals and pyrylium salt as the organic photocatalyst under visible light has been developed. Thus, various terminal keto thiocyanates were prepared without transition metals and oxidants in moderate to good yields. The simplicity, wide substrate scope and mild conditions feature its synthetic application capability.

KW - alkyl thiocyanation

KW - photocatalysis

KW - ring-opening functionalization

KW - synthetic methodology

KW - terminal thiocyanatoketone

UR - http://www.scopus.com/inward/record.url?scp=85193816958&partnerID=8YFLogxK

U2 - 10.1002/chem.202400453

DO - 10.1002/chem.202400453

M3 - Article

AN - SCOPUS:85193816958

SN - 0947-6539

VL - 30

JO - Chemistry - A European Journal

JF - Chemistry - A European Journal

IS - 36

M1 - e202400453

ER -

Organophotocatalytic Remote Thiocyanation Reaction via Ring-Opening Functionalization of Cycloalkanols

Abstract

Keywords

Access to Document

Other files and links

Fingerprint

Cite this