电化学氧化-碘促进丙酮α-H芳(烷)硒化制备α-芳(烷)硒基丙酮

doi:10.6023/cjoc202102024

有机化学 ›› 2021, Vol. 41 ›› Issue (9): 3726-3732.DOI: 10.6023/cjoc202102024 上一篇下一篇

所属专题：有机电合成虚拟专辑

研究简报

电化学氧化-碘促进丙酮α-H芳(烷)硒化制备α-芳(烷)硒基丙酮

易荣楠^a, 刘冬娴^a, 吴啟林^d, 赵明明^a, 王勇^b^,^*(), 王峥^c^,^*()

a 湖南警察学院刑事科学技术系长沙 410138
b 中南大学基础医学院法医学系长沙 410013
c 湖南科技学院化学与生物工程学院湖南永州 425100
d 长江师范学院化学化工学院重庆 408000

收稿日期:2021-02-08 修回日期:2021-03-20 发布日期:2021-06-07
通讯作者: 王勇, 王峥
基金资助:
湖南省自然科学基金(2019JJ40392); 湖南省自然科学基金(2019JJ50193)

Electrochemical Oxidated-Iodide Promoted α-H Aryl(alkyl)selenation of Acetone for the Preparation of α-Aryl(alkyl)selenoacetones

Rongnan Yi^a, Dongxian Liu^a, Qilin Wu^d, Mingming Zhao^a, Yong Wang^b(), Zheng Wang^c()

a Criminal Technology Department, Hunan Police Academy, Changsha 410138
b Department of Forensic Science, School of Basic Medical Science, Central South University, Changsha 410013
c Department of Chemistry, Hunan University of Science and Engineering, Yongzhou, Hunan 425100
d Department of Chemistry and Chemical Engineering, Yangtze Normal University, Chongqing 408000

Received:2021-02-08 Revised:2021-03-20 Published:2021-06-07
Contact: Yong Wang, Zheng Wang
Supported by:
Natural Science Foundation of Hunan Province(2019JJ40392); Natural Science Foundation of Hunan Province(2019JJ50193)

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摘要/Abstract

α-芳(烷)硒基酮作为重要的中间体在有机合成方面具有重要的应用. 报道了电化学氧化-碘促进下, 丙酮α-H芳(烷)硒化制备α-芳(烷)硒基丙酮化合物的方法, 本方法使用稳定、易得的二芳(烷)基二硒醚作为硒化试剂. 与已有的其它方法相比, 本方法具有反应条件温和、原子经济性高、底物适用范围广等优点, 为α-芳(烷)硒基丙酮化合物的制备提供了一条绿色、高效的合成路径.

关键词: 有机电合成, 碘促进反应, α-H芳(烷)硒化, α-芳(烷)硒基丙酮

α-Aryl(alkyl)selenyl ketones have been important intermediates in organic transformation. Here, a new route to α-aryl (alkyl) selenoacetones via the electrochemical oxidated iodide promoted α-H aryl(alkyl)selenation of acetone by using stable and easy available diaryl(alkyl)diselenides as selenide reagent is reported. Comparing to the previous methods, this strategy has the advantages of mild reaction conditions, high atom economy and wide functional groups tolerance, providing an efficient and green route to α-aryl (alkyl) selenoacetones.

Key words: electro-organic synthesis, iodide-promoted reaction, α-H aryl(alkyl)selenation, α-aryl(alkyl)selenoacetones

引用此文

易荣楠, 刘冬娴, 吴啟林, 赵明明, 王勇, 王峥. 电化学氧化-碘促进丙酮α-H芳(烷)硒化制备α-芳(烷)硒基丙酮[J]. 有机化学, 2021, 41(9): 3726-3732.

Rongnan Yi, Dongxian Liu, Qilin Wu, Mingming Zhao, Yong Wang, Zheng Wang. Electrochemical Oxidated-Iodide Promoted α-H Aryl(alkyl)selenation of Acetone for the Preparation of α-Aryl(alkyl)selenoacetones[J]. Chinese Journal of Organic Chemistry, 2021, 41(9): 3726-3732.

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电化学氧化-碘促进丙酮α-H芳(烷)硒化制备α-芳(烷)硒基丙酮

Electrochemical Oxidated-Iodide Promoted α-H Aryl(alkyl)selenation of Acetone for the Preparation of α-Aryl(alkyl)selenoacetones

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Entry	Variation from the standard reaction conditions	Yield^b/%
1	None	92
2	C(+)\|Pt(–) instead of Pt(+)\|Pt(–)	85
3	Ni (+)\|Pt(–) instead of Pt(+)\|Pt(–)	88
4	RVC(+)\|Pt(–) instead of Pt(+)\|Pt(–)	86
5	C(+)\|C(–) instead of Pt(+)\|Pt(–)	78
6	RVC (+)\|RVC(–) instead of Pt(+)\|Pt(–)	81
7	n-Bu₄NI instead of KI	82
8	NH₄I instead of KI	85
9	NaI instead of KI	80
10	I₂instead of KI, no electric current	24
11	NH₄Br instead of KI	52
12	LiBF₄ instead of KI	51
13	ⁿBu₄NBF₄ instead of KI	35
14	KI (25 mol%) instead of KI (50 mol%), 9 h	78
15	No electric current	N. R.
16	3 mA instead of 6 mA, 9 h	71
17	12 mA instead of 6 mA	83
18	12 mA instead of 6 mA, 3 h	60

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