Palladium-Catalyzed Deuterodehalogenation of Halogenated Aryl Triflates Using Isopropanol‑d8 as the Deuterium Source

Miao Wang; Wai Hang Pang; On Ying Yuen; Shan Shan Ng; Chau Ming So

doi:10.1021/acs.orglett.3c03281

Palladium-Catalyzed Deuterodehalogenation of Halogenated Aryl Triflates Using Isopropanol‑d₈ as the Deuterium Source

Miao Wang
, Wai Hang Pang
, On Ying Yuen
, Shan Shan Ng
, Chau Ming So

Research output: Journal article publication › Journal article › Academic research › peer-review

6 Citations (Scopus)

Abstract

In this study, a novel and efficient Pd-catalyzed chemoselective deuterodehalogenation reaction of halogenated aryl triflates was developed using isopropanol-d₈ as the deuterium source. This chemoselective reaction afforded an unconventional chemoselectivity order of C−Br > C−Cl > C−OTf. This catalytic system was successfully applied to chemoselective hydrodehalogenation of chloroaryl triflates, providing excellent C−Cl chemoselectivity over C−OTf.

Original language	English
Pages (from-to)	8429-8433
Number of pages	5
Journal	Organic Letters
Volume	25
Issue number	47
DOIs	https://doi.org/10.1021/acs.orglett.3c03281
Publication status	Published - 17 Nov 2023

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/acs.orglett.3c03281

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title = "Palladium-Catalyzed Deuterodehalogenation of Halogenated Aryl Triflates Using Isopropanol‑d8 as the Deuterium Source",

abstract = "In this study, a novel and efficient Pd-catalyzed chemoselective deuterodehalogenation reaction of halogenated aryl triflates was developed using isopropanol-d8 as the deuterium source. This chemoselective reaction afforded an unconventional chemoselectivity order of C−Br > C−Cl > C−OTf. This catalytic system was successfully applied to chemoselective hydrodehalogenation of chloroaryl triflates, providing excellent C−Cl chemoselectivity over C−OTf.",

author = "Miao Wang and Pang, \{Wai Hang\} and Yuen, \{On Ying\} and Ng, \{Shan Shan\} and So, \{Chau Ming\}",

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year = "2023",

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doi = "10.1021/acs.orglett.3c03281",

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T1 - Palladium-Catalyzed Deuterodehalogenation of Halogenated Aryl Triflates Using Isopropanol‑d8 as the Deuterium Source

AU - Wang, Miao

AU - Pang, Wai Hang

AU - Yuen, On Ying

AU - Ng, Shan Shan

AU - So, Chau Ming

PY - 2023/11/17

Y1 - 2023/11/17

N2 - In this study, a novel and efficient Pd-catalyzed chemoselective deuterodehalogenation reaction of halogenated aryl triflates was developed using isopropanol-d8 as the deuterium source. This chemoselective reaction afforded an unconventional chemoselectivity order of C−Br > C−Cl > C−OTf. This catalytic system was successfully applied to chemoselective hydrodehalogenation of chloroaryl triflates, providing excellent C−Cl chemoselectivity over C−OTf.

AB - In this study, a novel and efficient Pd-catalyzed chemoselective deuterodehalogenation reaction of halogenated aryl triflates was developed using isopropanol-d8 as the deuterium source. This chemoselective reaction afforded an unconventional chemoselectivity order of C−Br > C−Cl > C−OTf. This catalytic system was successfully applied to chemoselective hydrodehalogenation of chloroaryl triflates, providing excellent C−Cl chemoselectivity over C−OTf.

UR - https://www.scopus.com/pages/publications/85178651930

U2 - 10.1021/acs.orglett.3c03281

DO - 10.1021/acs.orglett.3c03281

M3 - Journal article

C2 - 37975627

AN - SCOPUS:85178651930

SN - 1523-7060

VL - 25

SP - 8429

EP - 8433

JO - Organic Letters

JF - Organic Letters

IS - 47

ER -

Palladium-Catalyzed Deuterodehalogenation of Halogenated Aryl Triflates Using Isopropanol‑d₈ as the Deuterium Source

Abstract

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