Preparation of a Highly Congested Carbazoyl-Derived P,N-Type Phosphine Ligand for Acetone Monoarylations

Wai Chung Fu; Zhongyuan Zhou; Fuk Yee Kwong

doi:10.1021/acs.organomet.6b00154

Preparation of a Highly Congested Carbazoyl-Derived P,N-Type Phosphine Ligand for Acetone Monoarylations

Wai Chung Fu, Zhongyuan Zhou, Fuk Yee Kwong^*

^*Corresponding author for this work

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

24 Citations (Scopus)

Abstract

We report a newly developed carbazoyl-derived P,N-type phosphine ligand (L1) for the monoarylation of acetone with aryl chlorides. The proposed Pd(dba)₂/L1 catalyst exhibited remarkable catalytic reactivity toward highly electron rich and sterically congested aryl chlorides, with catalyst loading as low as 0.1 mol % of Pd along with excellent chemoselectivity. A reaction rate study of the system using electronically diverse aryl chlorides determined the mechanisms regarding the rate-limiting steps in this reaction. The oxidative addition adduct of Pd-PhenCar-Phos with p-chlorotoluene showed the participation of N–Pd coordination in the metal complex. The isolated palladium complex C1 could be utilized as a precatalyst in the transformation and achieved performance comparable to that of the in situ generated palladium species. © 2016 American Chemical Society

Original language	English
Pages (from-to)	1553-1558
Number of pages	6
Journal	Organometallics
Volume	35
Issue number	10
Online published	31 Mar 2016
DOIs	https://doi.org/10.1021/acs.organomet.6b00154
Publication status	Published - 23 May 2016
Externally published	Yes

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title = "Preparation of a Highly Congested Carbazoyl-Derived P,N-Type Phosphine Ligand for Acetone Monoarylations",

abstract = "We report a newly developed carbazoyl-derived P,N-type phosphine ligand (L1) for the monoarylation of acetone with aryl chlorides. The proposed Pd(dba)2/L1 catalyst exhibited remarkable catalytic reactivity toward highly electron rich and sterically congested aryl chlorides, with catalyst loading as low as 0.1 mol % of Pd along with excellent chemoselectivity. A reaction rate study of the system using electronically diverse aryl chlorides determined the mechanisms regarding the rate-limiting steps in this reaction. The oxidative addition adduct of Pd-PhenCar-Phos with p-chlorotoluene showed the participation of N–Pd coordination in the metal complex. The isolated palladium complex C1 could be utilized as a precatalyst in the transformation and achieved performance comparable to that of the in situ generated palladium species. {\textcopyright} 2016 American Chemical Society",

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T1 - Preparation of a Highly Congested Carbazoyl-Derived P,N-Type Phosphine Ligand for Acetone Monoarylations

AU - Fu, Wai Chung

AU - Zhou, Zhongyuan

AU - Kwong, Fuk Yee

PY - 2016/5/23

Y1 - 2016/5/23

N2 - We report a newly developed carbazoyl-derived P,N-type phosphine ligand (L1) for the monoarylation of acetone with aryl chlorides. The proposed Pd(dba)2/L1 catalyst exhibited remarkable catalytic reactivity toward highly electron rich and sterically congested aryl chlorides, with catalyst loading as low as 0.1 mol % of Pd along with excellent chemoselectivity. A reaction rate study of the system using electronically diverse aryl chlorides determined the mechanisms regarding the rate-limiting steps in this reaction. The oxidative addition adduct of Pd-PhenCar-Phos with p-chlorotoluene showed the participation of N–Pd coordination in the metal complex. The isolated palladium complex C1 could be utilized as a precatalyst in the transformation and achieved performance comparable to that of the in situ generated palladium species. © 2016 American Chemical Society

AB - We report a newly developed carbazoyl-derived P,N-type phosphine ligand (L1) for the monoarylation of acetone with aryl chlorides. The proposed Pd(dba)2/L1 catalyst exhibited remarkable catalytic reactivity toward highly electron rich and sterically congested aryl chlorides, with catalyst loading as low as 0.1 mol % of Pd along with excellent chemoselectivity. A reaction rate study of the system using electronically diverse aryl chlorides determined the mechanisms regarding the rate-limiting steps in this reaction. The oxidative addition adduct of Pd-PhenCar-Phos with p-chlorotoluene showed the participation of N–Pd coordination in the metal complex. The isolated palladium complex C1 could be utilized as a precatalyst in the transformation and achieved performance comparable to that of the in situ generated palladium species. © 2016 American Chemical Society

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U2 - 10.1021/acs.organomet.6b00154

DO - 10.1021/acs.organomet.6b00154

M3 - RGC 21 - Publication in refereed journal

SN - 0276-7333

VL - 35

SP - 1553

EP - 1558

JO - Organometallics

JF - Organometallics

IS - 10

ER -

Preparation of a Highly Congested Carbazoyl-Derived P,N-Type Phosphine Ligand for Acetone Monoarylations

Abstract

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