A Method for the Synthesis of Deuterated Benzoins Catalyzed by N-Heterocyclic Carbene

doi:10.6023/cjoc202210005

Chinese Journal of Organic Chemistry ›› 2023, Vol. 43 ›› Issue (4): 1510-1516.DOI: 10.6023/cjoc202210005 Previous Articles Next Articles

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一种N-杂环卡宾催化合成氘代苯偶姻的方法

张心予, 耿慧慧, 张士磊, 王卫^*(), 陈晓蓓^*()

华东理工大学药学院上海市细胞代谢光遗传学技术前沿科学研究基地上海市新药设计重点实验室生物反应器工程国家重点实验室上海 200237

收稿日期:2022-10-06 修回日期:2022-11-20 发布日期:2022-12-07
通讯作者: 王卫, 陈晓蓓
基金资助:
国家自然科学基金(22071053); 国家自然科学基金(22271206); 上海市细胞代谢光遗传学技术前沿科学研究基地(上海市教育委员会, grant 2021 Sci & Tech 03-28(上海市教育委员会); 上海市细胞代谢光遗传学技术前沿科学研究基地(上海市教育委员会, grant 2021 Sci & Tech 03-28(grant 2021 Sci & Tech 03-28); 以及江苏省高校重点学科建设(PAPD)

A Method for the Synthesis of Deuterated Benzoins Catalyzed by N-Heterocyclic Carbene

Xinyu Zhang, Huihui Geng, Shilei Zhang, Wei Wang(), Xiaobei Chen()

Shanghai Frontiers Science Center of Optogenetic Techniques for Cell Metabolism, Shanghai Key Laboratory of New Drug Design, and State Key Laboratory of Bioengineering Reactor, School of Pharmacy, East China University of Science & Technology, Shanghai 200237

Received:2022-10-06 Revised:2022-11-20 Published:2022-12-07
Contact: Wei Wang, Xiaobei Chen
Supported by:
National Natural Science Foundation of China(22071053); National Natural Science Foundation of China(22271206); Shanghai Frontiers Science Center of Optogenetic Techniques for Cell Metabolism(grant 2021 Sci & Tech 03-28); Priority Academic Program Development of Jiangsu Higher Education Institutions(PAPD); Shanghai Frontiers Science Center of Optogenetic Techniques for Cell Metabolism(Shanghai Municipal Education Commission)

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Abstract

An efficient method has been developed for the synthesis of deuterated benzoins from two molecules of aldehydes under the catalysis of N-heterocyclic carbene by using D₂O as the deuterium source, providing the products with deuterium selectively incorporated at the α-position of ketone group. The method features simple operation and mild reaction conditions, and a variety of aromatic aldehyde substrates could afford products with high deuterium incorporation.

Key words: deuteration, deuteroxide, benzoin condensation, N-heterocyclic carbene, organocatalysis

Cite this article

Xinyu Zhang, Huihui Geng, Shilei Zhang, Wei Wang, Xiaobei Chen. A Method for the Synthesis of Deuterated Benzoins Catalyzed by N-Heterocyclic Carbene[J]. Chinese Journal of Organic Chemistry, 2023, 43(4): 1510-1516.

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Entry	Catalyst	Yield^b/%	D^c/%	ee^d/%
1	3a	58	75	—
2	3b	52	98	—
3	3c	55	98	—
4	3d	38	98	—
5	3e	54	95	<5
6	3f	51	98	—
7	3g	78	95	<5
8	3h	20	96	<5
9	3i	35	98	<5
10	3j	20	98	<5
11	3k	78	95	<5
12	3l	51	99	<5
13^e	3l	74	99	<5

Entry	Catalyst	Yield^b/%	D^c/%	ee^d/%
1	3a	58	75	—
2	3b	52	98	—
3	3c	55	98	—
4	3d	38	98	—
5	3e	54	95	<5
6	3f	51	98	—
7	3g	78	95	<5
8	3h	20	96	<5
9	3i	35	98	<5
10	3j	20	98	<5
11	3k	78	95	<5
12	3l	51	99	<5
13^e	3l	74	99	<5

一种N-杂环卡宾催化合成氘代苯偶姻的方法

A Method for the Synthesis of Deuterated Benzoins Catalyzed by N-Heterocyclic Carbene

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