t-BuOK促进的还原脱砜/脱氢反应: 选择性合成2-取代的1,3-共轭二烯及其应用

doi:10.6023/cjoc202102025

有机化学 ›› 2021, Vol. 41 ›› Issue (8): 3144-3156.DOI: 10.6023/cjoc202102025 上一篇下一篇

研究论文

t-BuOK促进的还原脱砜/脱氢反应: 选择性合成2-取代的1,3-共轭二烯及其应用

孙佳兵^a, 苗涛^a^,^*(), 李品华^a, 王磊^a^,^b^,^c^,^*()

a 淮北师范大学化学与材料科学学院绿色和精准合成化学及应用教育部重点实验室安徽淮北 235000
b 台州学院医药化工与材料工程学院浙江台州 318000
c 中国科学院上海有机化学研究所金属有机化学国家重点实验室上海 200032

收稿日期:2021-02-09 修回日期:2021-05-07 发布日期:2021-05-25
通讯作者: 苗涛, 王磊
基金资助:
国家自然科学基金(21772062); 国家自然科学基金(22071171); 国家自然科学基金(21602072); 安徽省高校自然科学基金(KJ2019ZD66)

t-BuOK-Mediated Reductive Desulfonylation/Dehydrogenation for the Synthesis of 2-Substituted 1,3-Dienes and Their [4+2] Cycloaddition Reactions

Jiabing Sun^a, Tao Miao^a(), Pinhua Li^a, Lei Wang^a^,^b^,^c()

a Key Laboratory of Green and Precise Synthetic Chemistry and Applications, Ministry of Education; School of Chemistry and Materials Science, Huaibei Normal University, Huabei, Anhui 235000
b Advanced Research Institute and Department of Chemistry, Taizhou University, Taizhou, Zhejiang 318000
c State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032

Received:2021-02-09 Revised:2021-05-07 Published:2021-05-25
Contact: Tao Miao, Lei Wang
Supported by:
National Natural Science Foundation of China(21772062); National Natural Science Foundation of China(22071171); National Natural Science Foundation of China(21602072); Anhui University Natural Science Research Project(KJ2019ZD66)

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摘要/Abstract

发展了一种叔丁醇钾促进的(Z)-C6-乙烯基砜基菲啶的脱砜、脱氢串联反应, 用于选择性地合成1,3-共轭二烯. 该反应无需过渡金属催化剂, 底物适用范围广, 以良好的收率得到相应的目标产物, 为菲啶官能化的1,3-共轭二烯的合成提供了新颖和有效的方法. 此外, 通过与富马腈的[4+2]环加成反应, 实现了1,3-共轭二烯的合成应用.

关键词: 叔丁醇钾, 脱砜反应, 1,3-共轭二烯, 环加成反应

A t-BuOK-mediated desulfonylation/dehydrogenation cascade reaction of (Z)-C6-(vinyl sulfone)phenanthridines is described. This process provides a novel and efficient strategy for the synthesis of 1,3-dienes with phenanthridinyl units in good yields under transition-metal-free conditions. Furthermore, the application of the generated 1,3-dienes in the [4+2] cycloaddition has been demonstrated by reacting with dienophiles such as fumaronitrile in a two-step procedure.

Key words: t-BuOK, desulfonylation, 1,3-conjugated dienes, cycloaddition reactions

引用此文

孙佳兵, 苗涛, 李品华, 王磊. t-BuOK促进的还原脱砜/脱氢反应: 选择性合成2-取代的1,3-共轭二烯及其应用[J]. 有机化学, 2021, 41(8): 3144-3156.

Jiabing Sun, Tao Miao, Pinhua Li, Lei Wang. t-BuOK-Mediated Reductive Desulfonylation/Dehydrogenation for the Synthesis of 2-Substituted 1,3-Dienes and Their [4+2] Cycloaddition Reactions[J]. Chinese Journal of Organic Chemistry, 2021, 41(8): 3144-3156.

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图/表 7

Scheme 1. Synthetic strategies for the construction of conjugated dienes

Entry	Base	Solvent	Yield^b/%
1	t-BuOK	CH₂Cl₂	40
2	t-BuOK	THF	87
3	t-BuOK	1,4-Dioxane	58
4	t-BuOK	CH₃CN	41
5	t-BuOK	Toluene	17
6	t-BuOK	DMF	30
7	t-BuOK	Acetone	41
8	t-BuOK	DMSO	0
9	t-BuOK	DCE	0
10	t-BuONa	THF	36
11	K₂CO₃	THF	0
12	Na₂CO₃	THF	0
13	Cs₂CO₃	THF	0
14	Et₃N	THF	0
15	Pyridine	THF	0
16	t-BuOK	THF	86 ^c
17	t-BuOK	THF	85 ^d
18	t-BuOK	THF	58 ^e
19	t-BuOK	THF	60 ^f

Table 1. Optimization of reaction conditionsa

Table 2. Scope of phenanthridine moiety in the substratesa

Table 3. Scope of (Z)-C6-(vinyl sulfone)phenanthridines with alkyl chaina

Table 4. Applications of 1,3-dienes by reacting with fumaronitrilea

Scheme 2. Control experiments

Scheme 3. Proposed mechanism

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t-BuOK促进的还原脱砜/脱氢反应: 选择性合成2-取代的1,3-共轭二烯及其应用

t-BuOK-Mediated Reductive Desulfonylation/Dehydrogenation for the Synthesis of 2-Substituted 1,3-Dienes and Their [4+2] Cycloaddition Reactions

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