E-Stereospecific 1,1-Carboboration of Terminal Arylalkynes with [IB(C6F5)3]–

doi:10.6023/cjoc202205029

Chinese Journal of Organic Chemistry ›› 2023, Vol. 43 ›› Issue (1): 338-344.DOI: 10.6023/cjoc202205029 Previous Articles Next Articles

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卤素阴离子催化的立体可控炔烃碳硼化反应研究

田冲^a, 孙奇^b, 王俊锋^b, 陈俏^a, 温志国^a, Maxim Borzov^a, 聂万丽^a^,^*()

a 乐山师范学院新能源材料与化学学院天然产物化学与小分子催化四川省高校重点实验室四川乐山 614000
b 中国航天科工集团第六研究院呼和浩特 010076

收稿日期:2022-05-18 修回日期:2022-07-20 发布日期:2022-08-25
通讯作者: 聂万丽
基金资助:
国家自然科学基金(21542011); 四川省科技厅计划(2020YJ0358); 乐山师范学院科研(DGZZ202018); 乐山师范学院科研(TRCWYFZCH2019006); 乐山师范学院科研(2021SSDJS015); 乐山师范学院科研(2021SSDJS016)

E-Stereospecific 1,1-Carboboration of Terminal Arylalkynes with [IB(C₆F₅)₃]^–

Chong Tian^a, Qi Sun^b, Junfeng Wang^b, Qiao Chen^a, Zhiguo Wen^a, Maxim Borzov^a, Wanli Nie^a()

a Sichuan Province Key Laboratory of Natural Products and Small Molecule Synthesis, Chemical Department of Leshan Normal University, Leshan, Sichuan 614000
b The 6th Research Institute of China Aerospace Science and Industry Corporation Limited, Hohho 010076

Received:2022-05-18 Revised:2022-07-20 Published:2022-08-25
Contact: Wanli Nie
Supported by:
National Natural Science Foundation of China(21542011); Science and Technology Department of Sichuan Province(2020YJ0358); Scientific Research Fund of Leshan Normal University(DGZZ202018); Scientific Research Fund of Leshan Normal University(TRCWYFZCH2019006); Scientific Research Fund of Leshan Normal University(2021SSDJS015); Scientific Research Fund of Leshan Normal University(2021SSDJS016)

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Abstract

The difunctionalization of alkenes and alkynes is a simple and powerful strategy for the synthesis of various organic compounds and has been used to synthesize various important natural products, drug molecules and fine chemical products. The different effects of halo anions, substrates, solvents, temperature and reaction time to the stereospecific and reactivities of 1,1-carboborations of alkynes and B(C₆F₅)s were studied, meanwhile the corresponding catalytic mechanisum has been expoled. A convenient large-scale preparation method for the stereoselective (E)-1,1-carboboration products has been developed. The catalytic reactivities of ring-opening polymerization of cyclohexene oxide (CHO) have also been explored with different stereo-carboboranes isolated from 1,1-carboboration reaction, and it is noted that the stereospecificity E- or Z- has shown ambiguously different activities. To develop a stereo-specific approach in the synthesis of vinylboranes will not only be very important for the difunctionalization of alkenes and alkynes, but also for the novel stereospecificity organoborons.

Key words: 1,1-carboboration, stereospecificity, alkynes, borane, reactivity

Cite this article

Chong Tian, Qi Sun, Junfeng Wang, Qiao Chen, Zhiguo Wen, Maxim Borzov, Wanli Nie. E-Stereospecific 1,1-Carboboration of Terminal Arylalkynes with [IB(C₆F₅)₃]^–[J]. Chinese Journal of Organic Chemistry, 2023, 43(1): 338-344.

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Fig. & Tab. 6

References 60

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Entry	Alkynes	[X^–] (X∶BCF)	2 (Z∶E)^a
1	1a	A (1∶1)	2a (>1∶99)
2	1a	B (1∶1)	2a (>1∶99)
3	1a	C (1∶1)	2a (1∶1)
4	1a	D (1∶1)	2a (1∶1)
5	1b	B (1∶1)	2b (>1∶99)
6	1c	B (1∶1)	2c (>1∶99)
7	1a	B (1∶5)	2a (1∶10)
8	1b	B (1∶5)	2b (1∶17)
9	1c	B (1∶5)	2c (1∶22)
10	1a^b	B (1∶5)	2a (>1∶99)
11	1b^b	B (1∶5)	2b (>1∶99)
12	1c^b	B (1∶5)	2c (>1∶99)
13	1d^b	B (1∶5)	2d (>1∶99)
14	1e^b	B (1∶5)	2e (1∶14)
15	1f^b	B (1∶5)	2f (1∶1)
16	1g^b	B (1∶5)	2g (1∶3)
17	1h^b	B (1∶5)	2h (1∶6)
18	1i^b	B (1∶5)	2i (1∶3)
19	1j	B (1∶1)	2j (1∶1)
20	1k	B (1∶1)	2k (1∶3)
21	1l	B (1∶1)	2l (1∶4)

Entry	Alkynes	[X^–] (X∶BCF)	2 (Z∶E)^a
1	1a	A (1∶1)	2a (>1∶99)
2	1a	B (1∶1)	2a (>1∶99)
3	1a	C (1∶1)	2a (1∶1)
4	1a	D (1∶1)	2a (1∶1)
5	1b	B (1∶1)	2b (>1∶99)
6	1c	B (1∶1)	2c (>1∶99)
7	1a	B (1∶5)	2a (1∶10)
8	1b	B (1∶5)	2b (1∶17)
9	1c	B (1∶5)	2c (1∶22)
10	1a^b	B (1∶5)	2a (>1∶99)
11	1b^b	B (1∶5)	2b (>1∶99)
12	1c^b	B (1∶5)	2c (>1∶99)
13	1d^b	B (1∶5)	2d (>1∶99)
14	1e^b	B (1∶5)	2e (1∶14)
15	1f^b	B (1∶5)	2f (1∶1)
16	1g^b	B (1∶5)	2g (1∶3)
17	1h^b	B (1∶5)	2h (1∶6)
18	1i^b	B (1∶5)	2i (1∶3)
19	1j	B (1∶1)	2j (1∶1)
20	1k	B (1∶1)	2k (1∶3)
21	1l	B (1∶1)	2l (1∶4)

Entry	[B]	[CHO]∶1	Conv./%	M_n/(kg•mol^–1)	PDI
1	BCF	50000∶1	75.5	1.17	1.98
2	(Z/E)-2a	50000∶1	66.0	1.06	2.01
3	(Z)-2a	50000∶1	81.8	1.42	2.00
4	(E)-2a	5000∶1	71.4	4.91	2.63
5	(Z/E)-2b	50000∶1	75.7	1.37	1.90
6	(Z)-2b	50000∶1	77.8	1.42	2.07
7	(E)-2b	5000∶1	77.6	5.52	1.73

Entry	[B]	[CHO]∶1	Conv./%	M_n/(kg•mol^–1)	PDI
1	BCF	50000∶1	75.5	1.17	1.98
2	(Z/E)-2a	50000∶1	66.0	1.06	2.01
3	(Z)-2a	50000∶1	81.8	1.42	2.00
4	(E)-2a	5000∶1	71.4	4.91	2.63
5	(Z/E)-2b	50000∶1	75.7	1.37	1.90
6	(Z)-2b	50000∶1	77.8	1.42	2.07
7	(E)-2b	5000∶1	77.6	5.52	1.73

卤素阴离子催化的立体可控炔烃碳硼化反应研究

E-Stereospecific 1,1-Carboboration of Terminal Arylalkynes with [IB(C₆F₅)₃]^–

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