Efficient Construction of Chiral Binaphthalene-Core Phosphepine Compounds Using Palladium-Catalyzed C—P Coupling Reactions

doi:10.6023/cjoc202404004

Chinese Journal of Organic Chemistry ›› 2024, Vol. 44 ›› Issue (12): 3771-3783.DOI: 10.6023/cjoc202404004 Previous Articles Next Articles

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钯催化C—P键偶联反应高效构建手性联二萘基磷杂七元环化合物

王崔颖^b, 张颖^b, 郑家练^b, 袁佳^a^,^b^,^*(), 孟思璇^b, 陈建^b, 余广鳌^b^,^*()

a 武汉纺织大学省部共建纺织新材料与先进加工技术国家重点实验室武汉 430200
b 华中师范大学化学学院绿色农药全国重点实验室传感技术与健康国家级智能生物国际联合研究中心武汉 430079

收稿日期:2024-04-02 修回日期:2024-05-16 发布日期:2024-06-24
基金资助:
国家自然科学基金(22371084); 国家自然科学基金(21072071); 国家自然科学基金(21472060); 国家自然科学基金(21772058); 高等学校学科创新引智计划(111计划); 高等学校学科创新引智计划(B17019); 华中师范大学中央高校基本科研业务费专项资金(CCNU17CG0011); 华中师范大学中央高校基本科研业务费专项资金(CCNU17KYZHSY07); 华中师范大学中央高校基本科研业务费专项资金(CCNU18KYZHSY06)

Efficient Construction of Chiral Binaphthalene-Core Phosphepine Compounds Using Palladium-Catalyzed C—P Coupling Reactions

Cuiying Wang^b, Ying Zhang^b, Jia-Lian Zheng^b, Jia Yuan^a^,^b^,^*(), Sixuan Meng^b, Jian Chen^b, Guang-Ao Yu^b^,^*()

a State Key Laboratory of New Textile Materials and Advanced Processing Technologies, Wuhan Textile University, Wuhan 430200
b International Joint Research Center for Intelligent Biosensor Technology and Health, National Key Laboratory of Green Pesticides, College of Chemistry, Central China Normal University, Wuhan 430079

Received:2024-04-02 Revised:2024-05-16 Published:2024-06-24
Contact: *E-mail:jyuan@wtu.edu.cn;yuguang@mail.ccnu.edu.cn
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)

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Abstract

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

Cite this article

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.

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Fig. & Tab. 7

Scheme 1. Synthesis of chiral binaphthalene-core monophosphepine ligands

Entry	Ligand	Base	Time/h	T/℃	Conversion^b/%
1	dppf	^tBuONa	16	110	85
2	dippf	^tBuONa	16	110	100
3	dippf	Cs₂CO₃	16	110	6
4	dippf	K₃PO₄	16	110	17
5	dippf	KF	16	110	15
6	dippf	^tBuONa	8	110	48
7	dippf	^tBuONa	72	50	19
8	No	^tBuONa	16	110	50
9^c	dippf	^tBuONa	16	110	100 (91^d, 97% ee)

Table 1. Optimization of reaction conditionsa

Table 2. Substrate scope of the C—P coupling reaction of aryl halides with (R)-1a

Table 3. Substrate scope of the C—P coupling reaction of heteroaryl halides with (R)-1a

Scheme 2. Reaction of (R)-7 with benzyl bromide

Figure 1. Molecular structures of (R)-7, (R)-23, and (R)-30 ORTEP (Oak Ridge Thermal Ellipsoid Plot) drawings of (R)-7, (R)-23, and (R)-30 with 30% ellipsoid probability. Hydrogen atoms have been omitted for clarity

Scheme 3. Synthesis of (R)-1

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钯催化C—P键偶联反应高效构建手性联二萘基磷杂七元环化合物

Efficient Construction of Chiral Binaphthalene-Core Phosphepine Compounds Using Palladium-Catalyzed C—P Coupling Reactions

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Fig. & Tab. 7

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