Electrochemical Allylic Alkylation of Morita-Baylis-Hillman Adducts and N-Hydroxyphthalimide Esters towards C(sp3)—C(sp3) Bond Formation

doi:10.6023/cjoc202209024

Chinese Journal of Organic Chemistry ›› 2023, Vol. 43 ›› Issue (4): 1574-1583.DOI: 10.6023/cjoc202209024 Previous Articles Next Articles

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Morita-Baylis-Hillman加合物和N-羟基邻苯二甲酰亚胺的电化学烯丙基烷基化形成C(sp³)—C(sp³)键

孙丽^a, 宋国欣^a, 韩家乐^a, 李继玉^a, 赵月^a, 杨璐华^a, 张峰^a, 赵坤^b, 毛比明^a^,^*()

a 山东第一医科大学(山东省医学科学院)药学与制药科学学院(药物研究所) 济南 250117
b 山东大学药学院天然产物化学生物学教育部重点实验室济南 250012

收稿日期:2022-09-19 修回日期:2022-10-19 发布日期:2022-11-15
通讯作者: 毛比明
基金资助:
国家自然科学基金(22101156); 国家自然科学基金(22101154); 山东省自然科学基金(ZR2021QB032); 山东省自然科学基金(ZR2021QB038); 泰山学者工程专项经费资助项目

Electrochemical Allylic Alkylation of Morita-Baylis-Hillman Adducts and N-Hydroxyphthalimide Esters towards C(sp³)—C(sp³) Bond Formation

Li Sun^a, Guoxin Song^a, Jiale Han^a, Jiyu Li^a, Yue Zhao^a, Luhua Yang^a, Feng Zhang^a, Kun Zhao^b, Biming Mao^a()

a School of Parmacy and Pharmaceutical Science & Institute of Materia Medica, Shandong First Medical University & Shandong Academy of Medical Sciences, Jinan 250117
b Key Laboratory of Chemical Biology (Ministry of Education), School of Pharmaceutical Sciences, Shandong University, Jinan 250012

Received:2022-09-19 Revised:2022-10-19 Published:2022-11-15
Contact: Biming Mao
Supported by:
National Natural Science Foundation of China(22101156); National Natural Science Foundation of China(22101154); Natural Science Foundation of Shandong Province(ZR2021QB032); Natural Science Foundation of Shandong Province(ZR2021QB038); Taishan Scholar Youth Program of Shandong Province

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Abstract

A redox-free, electroreductive approach to achieve allylic alkylation by employing Morita-Baylis-Hillman (MBH) adducts is reported. A critical feature of this transformation is that neither external chemical oxidants nor metal catalysts are required. Alkyl radical produced by electron reduction with N-hydroxyphthalimide (NHP) esters, displaying broad tolerance of functional groups and alkene substitution patterns in high stereoselectivity and regioselectivity.

Key words: allylic alkylation, Morita-Baylis-Hillman (MBH) adducts, electroreductive approach

Cite this article

Li Sun, Guoxin Song, Jiale Han, Jiyu Li, Yue Zhao, Luhua Yang, Feng Zhang, Kun Zhao, Biming Mao. Electrochemical Allylic Alkylation of Morita-Baylis-Hillman Adducts and N-Hydroxyphthalimide Esters towards C(sp³)—C(sp³) Bond Formation[J]. Chinese Journal of Organic Chemistry, 2023, 43(4): 1574-1583.

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Entry		Variation from condition^a	Yield^b/%
1		None	90
2		CH₃CN instead of DMF	77
3		DMSO instead of DMF	48
4	ⁿBu₄NBF₄ instead of ⁿBu₄NHSO₄		67
5		Pt (－) instead of C (－)	41
6		Fe (－) instead of C (－)	43
7		Pt (+) instead of C (+)	58
8		I=4 mA, 135 min	88
9		I=8 mA, 68 min	72
10		1a 0.15 mmol	72
11		Boc instead of Ac	89
12		Air instead of Ar	67
13		No electric current	N.D.

Entry		Variation from condition^a	Yield^b/%
1		None	90
2		CH₃CN instead of DMF	77
3		DMSO instead of DMF	48
4	ⁿBu₄NBF₄ instead of ⁿBu₄NHSO₄		67
5		Pt (－) instead of C (－)	41
6		Fe (－) instead of C (－)	43
7		Pt (+) instead of C (+)	58
8		I=4 mA, 135 min	88
9		I=8 mA, 68 min	72
10		1a 0.15 mmol	72
11		Boc instead of Ac	89
12		Air instead of Ar	67
13		No electric current	N.D.

Morita-Baylis-Hillman加合物和N-羟基邻苯二甲酰亚胺的电化学烯丙基烷基化形成C(sp³)—C(sp³)键

Electrochemical Allylic Alkylation of Morita-Baylis-Hillman Adducts and N-Hydroxyphthalimide Esters towards C(sp³)—C(sp³) Bond Formation

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