Catalytic Properties of Sterically Shielded Carbene Complexes of Palladium in C–C and C–N Coupling Reactions of Haloarenes

IF 0.7 4区 化学 Q4 CHEMISTRY, MULTIDISCIPLINARY
V. Sh. Saberov, N. I. Korotkikh, A. S. Avksentiev, V. I. Yenya, G. F. Rayenko
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引用次数: 0

Abstract

New carbene complex catalysts based on palladium chloride, including PEPPSI-complexes (PEPPSI = Pyridine-Enhanced Precatalyst Preparation Stabilization and Initiation), have been synthesized. These catalysts show high efficiency in Buchwald–Hartwig C–N cross-coupling between aryl chlorides/bromides and amines, including sterically shielded reagents, and high efficiency in the Suzuki–Miyaura C–C cross-coupling reaction, where their use results in the formation of several tetra-ortho-substituted biaryls at very low amounts of catalyst under mild conditions. Modification of the catalyst structure to the PEPPSI complex leads to an unexpected decrease in activity in the Buchwald–Hartwig amination, in contrast to the Suzuki–Miyaura reaction, in which the PEPPSI complex showed greater activity in some cases.

Abstract Image

Abstract Image

卤代烃 C-C 和 C-N 偶联反应中钯的立体屏蔽碳烯配合物的催化特性
我们合成了基于氯化钯的新型碳烯络合物催化剂,包括 PEPPSI-络合物(PEPPSI = Pyridine-Enhanced Precatalyst Preparation Stabilization and Initiation)。这些催化剂在芳基氯化物/溴化物与胺(包括立体屏蔽试剂)之间的 Buchwald-Hartwig C-N 交叉偶联反应中表现出高效率,在 Suzukii-Miyaura C-C 交叉偶联反应中也表现出高效率。改变 PEPPSI 复合物的催化剂结构会导致布赫瓦尔德-哈特维格胺化反应的活性意外降低,这与铃木-宫浦反应形成鲜明对比,在某些情况下,PEPPSI 复合物显示出更高的活性。
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来源期刊
Theoretical and Experimental Chemistry
Theoretical and Experimental Chemistry CHEMISTRY, MULTIDISCIPLINARY-
CiteScore
1.60
自引率
10.00%
发文量
30
审稿时长
6-12 weeks
期刊介绍: Theoretical and Experimental Chemistry is a journal for the rapid publication of research communications and reviews on modern problems of physical chemistry such as: a) physicochemical bases, principles, and methods for creation of novel processes, compounds, and materials; b) physicochemical principles of chemical process control, influence of external physical forces on chemical reactions; c) physical nanochemistry, nanostructures and nanomaterials, functional nanomaterials, size-dependent properties of materials.
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