Site-selective deuteration at the α-position of enals by an amine and bis(phenylsulfonyl)methane co-catalyzed H/D exchange reaction

Pengfei Qian; Shilei Zhang; Fan Luo; Jiarui Wang; Xinyu Zhang; Xuejun Liu; Xiaodong Chen; Wei Wang; Xiaobei Chen

doi:10.1039/d2cc04959g

Site-selective deuteration at the α-position of enals by an amine and bis(phenylsulfonyl)methane co-catalyzed H/D exchange reaction

Pengfei Qian, Shilei Zhang, Fan Luo, Jiarui Wang, Xinyu Zhang, Xuejun Liu, Xiaodong Chen, Wei Wang, Xiaobei Chen

Pharmacology and Toxicology

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

2 Scopus citations

Abstract

An amine and bis(phenylsulfonyl)methane co-catalyzed hydrogen-deuterium exchange (HDE) method via a Michael-retro-Michael pathway for site-selective introduction of deuterium at the α-position of enals using D₂O as a deuterium source has been achieved. The mild, operationally simple protocol allows for high yielding and high level deuterium incorporation (up to 99%) for structurally diverse aromatic-derived enals and dienals.

Original language	English (US)
Journal	Chemical Communications
DOIs	https://doi.org/10.1039/d2cc04959g
State	Accepted/In press - 2022

ASJC Scopus subject areas

Electronic, Optical and Magnetic Materials
Ceramics and Composites
Metals and Alloys
Materials Chemistry
Surfaces, Coatings and Films
General Chemistry
Catalysis

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title = "Site-selective deuteration at the α-position of enals by an amine and bis(phenylsulfonyl)methane co-catalyzed H/D exchange reaction",

abstract = "An amine and bis(phenylsulfonyl)methane co-catalyzed hydrogen-deuterium exchange (HDE) method via a Michael-retro-Michael pathway for site-selective introduction of deuterium at the α-position of enals using D2O as a deuterium source has been achieved. The mild, operationally simple protocol allows for high yielding and high level deuterium incorporation (up to 99%) for structurally diverse aromatic-derived enals and dienals.",

author = "Pengfei Qian and Shilei Zhang and Fan Luo and Jiarui Wang and Xinyu Zhang and Xuejun Liu and Xiaodong Chen and Wei Wang and Xiaobei Chen",

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year = "2022",

doi = "10.1039/d2cc04959g",

language = "English (US)",

journal = "Chemical Communications",

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publisher = "Royal Society of Chemistry",

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TY - JOUR

T1 - Site-selective deuteration at the α-position of enals by an amine and bis(phenylsulfonyl)methane co-catalyzed H/D exchange reaction

AU - Qian, Pengfei

AU - Zhang, Shilei

AU - Luo, Fan

AU - Wang, Jiarui

AU - Zhang, Xinyu

AU - Liu, Xuejun

AU - Chen, Xiaodong

AU - Wang, Wei

AU - Chen, Xiaobei

PY - 2022

Y1 - 2022

N2 - An amine and bis(phenylsulfonyl)methane co-catalyzed hydrogen-deuterium exchange (HDE) method via a Michael-retro-Michael pathway for site-selective introduction of deuterium at the α-position of enals using D2O as a deuterium source has been achieved. The mild, operationally simple protocol allows for high yielding and high level deuterium incorporation (up to 99%) for structurally diverse aromatic-derived enals and dienals.

AB - An amine and bis(phenylsulfonyl)methane co-catalyzed hydrogen-deuterium exchange (HDE) method via a Michael-retro-Michael pathway for site-selective introduction of deuterium at the α-position of enals using D2O as a deuterium source has been achieved. The mild, operationally simple protocol allows for high yielding and high level deuterium incorporation (up to 99%) for structurally diverse aromatic-derived enals and dienals.

UR - http://www.scopus.com/inward/record.url?scp=85139739629&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=85139739629&partnerID=8YFLogxK

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DO - 10.1039/d2cc04959g

M3 - Article

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AN - SCOPUS:85139739629

SN - 1359-7345

JO - Chemical Communications

JF - Chemical Communications

ER -

Site-selective deuteration at the α-position of enals by an amine and bis(phenylsulfonyl)methane co-catalyzed H/D exchange reaction

Abstract

ASJC Scopus subject areas

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