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

68 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

Funding

We thank the Research Grants Council of Hong Kong (CRF: C5023-14G), General Research Fund (PolyU 153008/14P), and SKL of Chirosciences for financial support.

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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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day = "18",

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.

UR - https://www.scopus.com/pages/publications/84941896212

UR - https://www.scopus.com/pages/publications/84941896212#tab=impact

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

Abstract

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