Titanium-Catalyzed Synthesis of 1,1-Diborylalkanes from Aryl Alkenes

doi:10.6023/cjoc202309021

Chinese Journal of Organic Chemistry ›› 2024, Vol. 44 ›› Issue (2): 631-637.DOI: 10.6023/cjoc202309021 Previous Articles Next Articles

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钛催化的烯烃制备1,1-二硼化合物

李思达^a^,^b^,^c, 崔鑫^a, 舒兴中^b^,^*(), 吴立朋^a^,^d^,^*()

a 中国科学院兰州化学物理研究所羰基合成与选择氧化国家重点实验室兰州 730000
b 兰州大学化学化工学院功能有机分子化学国家重点实验室兰州 730000
c 中国科学院大学北京 100049
d 杭州师范大学材料与化学化工学院有机硅化学及材料技术教育部重点实验室杭州 311121

收稿日期:2023-09-21 修回日期:2023-10-04 发布日期:2023-10-12
作者简介:
^† 共同第一作者
基金资助:
国家自然科学基金(22271295); 及甘肃省自然科学基金重点(23JRRA606)

Titanium-Catalyzed Synthesis of 1,1-Diborylalkanes from Aryl Alkenes

Sida Li^a^,^b^,^c, Xin Cui^a, Xing-Zhong Shu^b(), Lipeng Wu^a^,^d()

a State Key Laboratory for Oxo Synthesis and Selective Oxidation, Lanzhou Institute of Chemical Physics, Chinese Academy of Sciences, Lanzhou 730000
b State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou 730000
c University of Chinese Academy of Sciences, Beijing 100049
d Key Laboratory of Organosilicon Chemistry and Material Technology, Ministry of Education, College of Material Chemistry and Chemical Engineering, Hangzhou Normal University, Hangzhou 311121

Received:2023-09-21 Revised:2023-10-04 Published:2023-10-12
Contact: * E-mail: shuxingzh@lzu.edu.cn; lipengwu@licp.cas.cn
About author:
^† These authors contributed equally to this work.
Supported by:
National Natural Science Foundation of China(22271295); Natural Science Foundation of Gansu Province Key Project(23JRRA606)

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Abstract

A milder and general atom-economical synthesis of 1,1-diborylalkanes from aryl alkenes with pinacolborane (HBpin) at room temperature is achieved. The key to success is using an earth-abundant titanium-based catalyst (Cp₂TiCl₂) with the help of lithium methoxide (MeOLi) as the activator. It is proposed that the in-situ formation of Ti-H species from Cp₂TiCl₂/MeOLi/HBpin system is the vital active species for the catalytic results.

Key words: titanium, alkene, 1,1-diboration, catalysis

Cite this article

Sida Li, Xin Cui, Xing-Zhong Shu, Lipeng Wu. Titanium-Catalyzed Synthesis of 1,1-Diborylalkanes from Aryl Alkenes[J]. Chinese Journal of Organic Chemistry, 2024, 44(2): 631-637.

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Fig. & Tab. 5

Scheme 1. Catalytic 1,1-diboration of alkenes using (a) B2pin2 as the boration reagent to avoid the reduction reactivity of HBpin and (b) HBpin as the boration reagent in the presence of excess amount H2-acceptor, and (c) our previous work using zirconium catalyst at 100 ℃ and (d) current work using more abundant and cheaper titanium catalyst at room temperature

Entry	Catalyst	Solvent	Yield^b/%
Entry	Catalyst	Solvent	3	4	5
1	CpTiCl₃	Toluene	3	28	18
2	Cp*TiCl₃	Toluene	14	41	34
3	IndTiCl₃	Toluene	0	56	2
4	Cp₂TiCl₂	Toluene	24	30	46
5	SiMe₂Cp₂TiCl₂	Toluene	4	41	12
6	Cp₂TiCl₂	Dioxane	8	56	36
7	Cp₂TiCl₂	MTBE	8	25	32
8	Cp₂TiCl₂	THF	9	71	20
9	Cp₂TiCl₂	Et₂O	8	24	68
10	Cp₂TiCl₂	Hexane	9	25	66
11	Cp₂TiCl₂	Neat	10	16	74

Table 1. Condition optimization of Ti-catalyzed direct synthesis of 1,1-diborylalkanes from alkenesa

Table 2. Substrate generality for titanium-catalyzed 1,1-diboration of various aryl al-kenesa

Figure 1. (A) 11B NMR spectrum of 0.1 mmol Cp2TiCl2, 0.2 mmol MeOLi and 0.2 mmol HBpin in 0.5 mL d6-benzene after stirred for 0.5 h, and (B) 1H NMR spectra of standard Cp2TiCl2, MeOLi sample in d6-benzene and the sequential addition of MeOLi and HBpin to d6-benzene solution of Cp2TiCl2

Scheme 2. Proposed reaction pathway to form the active Ti-H species, HBpin triggered 1-octene isomerization experiments and proposed reaction mechanism

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钛催化的烯烃制备1,1-二硼化合物

Titanium-Catalyzed Synthesis of 1,1-Diborylalkanes from Aryl Alkenes

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