Preparation of a Highly Congested Carbazoyl-Derived P,N-Type Phosphine Ligand for Acetone Monoarylations
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- 作者：Wai Chung Fu ; Zhongyuan Zhou ; Fuk Yee Kwong
- 刊名：Organometallics
- 出版年：2016
- 出版时间：May 23, 2016
- 年：2016
- 卷：35
- 期：10
- 页码：1553-1558
- 全文大小：422K
- 年卷期：0
- ISSN：1520-6041
文摘
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.