Design of an Indolylphosphine Ligand for Reductive Elimination-Demanding Monoarylation of Acetone Using Aryl Chlorides

Wai Chung Fu; Chau Ming So; Wing Kin Chow; On Ying Yuen; Fuk Yee Kwong

doi:10.1021/acs.orglett.5b02344

Design of an Indolylphosphine Ligand for Reductive Elimination-Demanding Monoarylation of Acetone Using Aryl Chlorides

Wai Chung Fu, Chau Ming So^*, Wing Kin Chow, On Ying Yuen, Fuk Yee Kwong^*

^*Corresponding author for this work

Research output: Journal Publications and Reviews › RGC 21 - Publication in refereed journal › peer-review

66 Citations (Scopus)

Abstract

The rational design of a phosphine ligand for the reductive elimination-demanding Pd-catalyzed mono-α-arylation of acetone is demonstrated and reported. The catalyst is tolerant of previously proven challenging electron-deficient aryl chlorides and provides excellent product yields with down to 0.1 mol % Pd. Preliminary investigations suggest that the rate-limiting step for the proposed system is the oxidative addition of aryl chlorides, in which it contradicts previous findings regarding the α-arylation of acetone with aryl halides. © 2015 American Chemical Society.

Original language	English
Pages (from-to)	4612-4615
Number of pages	4
Journal	Organic Letters
Volume	17
Issue number	18
Online published	9 Sept 2015
DOIs	https://doi.org/10.1021/acs.orglett.5b02344
Publication status	Published - 18 Sept 2015
Externally published	Yes

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title = "Design of an Indolylphosphine Ligand for Reductive Elimination-Demanding Monoarylation of Acetone Using Aryl Chlorides",

abstract = "The rational design of a phosphine ligand for the reductive elimination-demanding Pd-catalyzed mono-α-arylation of acetone is demonstrated and reported. The catalyst is tolerant of previously proven challenging electron-deficient aryl chlorides and provides excellent product yields with down to 0.1 mol % Pd. Preliminary investigations suggest that the rate-limiting step for the proposed system is the oxidative addition of aryl chlorides, in which it contradicts previous findings regarding the α-arylation of acetone with aryl halides. {\textcopyright} 2015 American Chemical Society.",

author = "Fu, {Wai Chung} and So, {Chau Ming} and Chow, {Wing Kin} and Yuen, {On Ying} and Kwong, {Fuk Yee}",

year = "2015",

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doi = "10.1021/acs.orglett.5b02344",

language = "English",

volume = "17",

pages = "4612--4615",

journal = "Organic Letters",

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T1 - Design of an Indolylphosphine Ligand for Reductive Elimination-Demanding Monoarylation of Acetone Using Aryl Chlorides

AU - Fu, Wai Chung

AU - So, Chau Ming

AU - Chow, Wing Kin

AU - Yuen, On Ying

AU - Kwong, Fuk Yee

PY - 2015/9/18

Y1 - 2015/9/18

N2 - The rational design of a phosphine ligand for the reductive elimination-demanding Pd-catalyzed mono-α-arylation of acetone is demonstrated and reported. The catalyst is tolerant of previously proven challenging electron-deficient aryl chlorides and provides excellent product yields with down to 0.1 mol % Pd. Preliminary investigations suggest that the rate-limiting step for the proposed system is the oxidative addition of aryl chlorides, in which it contradicts previous findings regarding the α-arylation of acetone with aryl halides. © 2015 American Chemical Society.

AB - The rational design of a phosphine ligand for the reductive elimination-demanding Pd-catalyzed mono-α-arylation of acetone is demonstrated and reported. The catalyst is tolerant of previously proven challenging electron-deficient aryl chlorides and provides excellent product yields with down to 0.1 mol % Pd. Preliminary investigations suggest that the rate-limiting step for the proposed system is the oxidative addition of aryl chlorides, in which it contradicts previous findings regarding the α-arylation of acetone with aryl halides. © 2015 American Chemical Society.

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UR - https://www.scopus.com/record/pubmetrics.uri?eid=2-s2.0-84941896212&origin=recordpage

U2 - 10.1021/acs.orglett.5b02344

DO - 10.1021/acs.orglett.5b02344

M3 - RGC 21 - Publication in refereed journal

SN - 1523-7060

VL - 17

SP - 4612

EP - 4615

JO - Organic Letters

JF - Organic Letters

IS - 18

ER -

Design of an Indolylphosphine Ligand for Reductive Elimination-Demanding Monoarylation of Acetone Using Aryl Chlorides

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