Comparative Screening of DalPhos/Ni Catalysts in C-N Cross-couplings of (Hetero)aryl Chlorides Enables Development of Aminopyrazole Cross-couplings with Amine Base

被引：9

作者：

Martinek, Nicole ^{[1
]}

Morrison, Kathleen M. M. ^{[1
]}

Field, Justin M. M. ^{[1
]}

Fisher, Samuel A. A. ^{[1
]}

Stradiotto, Mark ^{[1
]}

机构：

[1] Dalhousie Univ, Dept Chem, 6274 Coburg Rd,POB 15000, Halifax, NS B3H 4R2, Canada

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2023年 / 29卷 / 07期

基金：

加拿大自然科学与工程研究理事会;

关键词：

arylation; bisphosphine; catalyst screening; C-N cross-coupling; nickel; NICKEL PRECATALYST; AMINATION; ARYL; LIGAND; OPTIMIZATION; PERSPECTIVE; DERIVATIVES; DISCOVERY; ARYLATION; POTENT;

D O I：

10.1002/chem.202203394

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A systematic competitive evaluation of the DalPhos ligand family in nickel-catalyzed N-arylation chemistry is reported, involving primary (linear and branched) and secondary alkylamines, as well as a primary five-membered heteroarylamine (aminopyrazole), in combination with a diverse set of test electrophiles and bases (NaOtBu, K2CO3, DBU/NaTFA). In addition to providing optimal ligand/catalyst identification, and bringing to light methodology limitations (e. g., unwanted C-O cross-coupling with NaOtBu), our survey enabled the development of the first efficient catalyst system for heteroatom-dense C-N cross-coupling of aminopyrazoles and related nucleophiles with (hetero)aryl chlorides by use of an amine 'dual-base' system.

引用

页数：10

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