Deboronative Selenylation, Bromination, or Hydroxylation of Organic Boronic Acids Facilitated by Tetrabutylammonium Tribromide under Transition Metal-Free Conditions

doi:10.6023/cjoc202312023

Chinese Journal of Organic Chemistry ›› 2024, Vol. 44 ›› Issue (6): 1987-1997.DOI: 10.6023/cjoc202312023 Previous Articles Next Articles

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四丁基三溴化铵促进的有机硼酸在无过渡金属条件下的脱硼硒化、溴化和羟基化反应

田永盛^a, 魏斓枫^c, 黄嘉为^a, 韦玉^a, 徐亮^a^,^*(), 刘帅^b^,^*()

a 石河子大学化学化工学院/化工绿色过程省部共建国家重点实验室培育基地新疆石河子 832003
b 石河子大学兵团能源发展研究院新疆石河子 832003
c 新疆工程学院新疆煤矿灾害智能防控与应急重点实验室乌鲁木齐 830023

收稿日期:2023-12-24 修回日期:2024-01-17 发布日期:2024-02-19
基金资助:
国家自然科学基金(22061036); 国家自然科学基金(21963010)

Deboronative Selenylation, Bromination, or Hydroxylation of Organic Boronic Acids Facilitated by Tetrabutylammonium Tribromide under Transition Metal-Free Conditions

Yongsheng Tian^a, Lanfeng Wei^c, Jiawei Huang^a, Yu Wei^a, Liang Xu^a,*(), Shuai Liu^b,*()

a School of Chemistry and Chemical Engineering/State Key Laboratory Incubation Base for Green Processing of Chemical Enginering, Shihezi University, Shihezi, Xinjiang 832003
b Bintuan Energy Development Institute, Shihezi University, Shihezi, Xinjiang 832003
c Xinjiang Key Laboratory of Coal Mine Disasters Intelligent Prevention and Emergency Response, Xinjiang Institute of Engineering, Urumqi 830023

Received:2023-12-24 Revised:2024-01-17 Published:2024-02-19
Contact: * xuliang4423@shzu.edu.cn; liushuai0053@shzu.edu.cn
Supported by:
National Natural Science Foundation of China(22061036); National Natural Science Foundation of China(21963010)

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Abstract

Divergent approaches for the convenient ipso-functionalization of organic boronic acids are presented, capitalizing on tetrabutylammonium tribromide (TBATB) under different, yet transition metal-free conditions. Through these methods, a wide array of organoborons can be efficiently converted into their corresponding selenylated, brominated, or hydroxylated products in moderate to excellent yields. The versatility of this strategy lies in its transition metal-free conditions, simple operation, and step-economic pathways, offering a promising idea for the ipso-functionalization of organoborons

Key words: tetrabutylammonium tribromide, organic boronic acid, selenylation, bromination, hydroxylation, transition metal-free

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Yongsheng Tian, Lanfeng Wei, Jiawei Huang, Yu Wei, Liang Xu, Shuai Liu. Deboronative Selenylation, Bromination, or Hydroxylation of Organic Boronic Acids Facilitated by Tetrabutylammonium Tribromide under Transition Metal-Free Conditions[J]. Chinese Journal of Organic Chemistry, 2024, 44(6): 1987-1997.

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Fig. & Tab. 7

Scheme 1. Conversion of organoborate compound

Entry	Variation from the standard conditions	Yield^b/%
1	None	92
2	Without TBATB	N.R.^c
3	TBATB (10 mol%)	65
4	Without light (in dark)	90
5	Without O₂ (with Ar)	87
6	DMF instead of DMSO	31
7	MeCN instead of DMSO	17
8	MeOH instead of DMSO	29
9	Room temperature	47
10	80 ℃ instead of 100 ℃	79
11	90 ℃ instead of 100 ℃	85
12	10 h instead of 12 h	86
13	11 h instead of 12 h	90

Table 1. Optimization of the reaction condition for organoboric acid deboronative selenylation

Table 2. Substrate scope of deboronative selenylation

Table 3. Substrate scope of deboronative bromination

Table 4. Substrate scope of deboronative hydroxylation

Scheme 2. Phenylboronic acid pinacol ester deboronative selenylation reaction, gram-scale reaction and mechanism experiments

Scheme 3. Proposed mechanism of arylboronic acid deboronative selenylation reaction

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四丁基三溴化铵促进的有机硼酸在无过渡金属条件下的脱硼硒化、溴化和羟基化反应

Deboronative Selenylation, Bromination, or Hydroxylation of Organic Boronic Acids Facilitated by Tetrabutylammonium Tribromide under Transition Metal-Free Conditions

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