Chinese Journal of Organic Chemistry >
Efficient Construction of Chiral Binaphthalene-Core Phosphepine Compounds Using Palladium-Catalyzed C—P Coupling Reactions
Received date: 2024-04-02
Revised date: 2024-05-16
Online published: 2024-06-24
Supported by
the National Natural Science Foundation of China(22371084); the National Natural Science Foundation of China(21072071); the National Natural Science Foundation of China(21472060); the National Natural Science Foundation of China(21772058); Programme of Introducing Talents of Discipline to Universities(111 Project); Programme of Introducing Talents of Discipline to Universities(B17019); Self-Determined Research Funds of Central China Normal University from the Colleges’ Basic Research and Operation of Ministry of Education(CCNU17CG0011); Self-Determined Research Funds of Central China Normal University from the Colleges’ Basic Research and Operation of Ministry of Education(CCNU17KYZHSY07); Self-Determined Research Funds of Central China Normal University from the Colleges’ Basic Research and Operation of Ministry of Education(CCNU18KYZHSY06)
Binaphthalene-core phosphepine compounds with axial chirality belong to an important class of organocatalysts and ligands used in catalytic asymmetric synthesis. However, the number and application of these compounds have been limited due to the lack of efficient synthetic methods currently available to researchers. Herein, a simple and efficient palladium-catalyzed C—P cross-coupling reaction of enantiopure (R)-1 with a variety of aryl and heteroaryl halides is reported. The reaction provides access to a series of chiral binaphthalene-core phosphepine compounds using Pd(OAc)2/dippf as a catalyst, which allows most products to be formed in moderate to high yields (40%~92%) with excellent ee values (90%~99% ee).
Key words： Pd catalysis; chiral axially; binaphthalene; C—P coupling reactions
Cuiying Wang , Ying Zhang , Jia-Lian Zheng , Jia Yuan , Sixuan Meng , Jian Chen , Guang-Ao Yu . Efficient Construction of Chiral Binaphthalene-Core Phosphepine Compounds Using Palladium-Catalyzed C—P Coupling Reactions[J]. Chinese Journal of Organic Chemistry, 2024 , 44(12) : 3771 -3783 . DOI: 10.6023/cjoc202404004
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