铑催化定位基促进芳环C—H键和碳酸亚乙烯酯的缩合得到异香豆素

doi:10.6023/cjoc202106023

有机化学 ›› 2022, Vol. 42 ›› Issue (1): 242-248.DOI: 10.6023/cjoc202106023 上一篇下一篇

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铑催化定位基促进芳环C—H键和碳酸亚乙烯酯的缩合得到异香豆素

王璐^a, 邵莺^a, 陈帆^b, 钱鹏程^b^,^*(), 成江^a^,^b^,^*()

a 常州大学石油化工学院江苏常州 213164
b 温州大学化学与材料工程学院浙江温州 325035

收稿日期:2021-06-10 修回日期:2021-07-14 发布日期:2021-09-02
通讯作者: 钱鹏程, 成江
基金资助:
国家自然科学基金(21971025); 先进催化与绿色制造协同创新中心资助项目; 江苏省先进催化材料与技术重点实验室(BM2012110); 温州市科技局基金(W20170003)

Rhodium-Catalyzed Directing Group-Assisted Annulation of Arene C—H Bond with Vinylene Carbonate toward Isocoumarins

Lu Wang^a, Ying Shao^a, Fan Chen^b, Pengcheng Qian^b(), Jiang Cheng^a^,^b()

a School of Petrochemical Engineering, Changzhou University, Changzhou, Jiangsu 213164
b College of Chemistry & Materials Engineering, Wenzhou University, Wenzhou, Zhejiang 325035

Received:2021-06-10 Revised:2021-07-14 Published:2021-09-02
Contact: Pengcheng Qian, Jiang Cheng
Supported by:
National Natural Science Foundation of China(21971025); Advanced Catalysis and Green Manufacturing Collaborative Innovation Center; “Innovation & Entrepreneurship Talents” Introduction Plan of Jiangsu Province, the Jiangsu Key Laboratory of Advanced Catalytic Materials & Technology(BM2012110); Foundation of Wenzhou Science & Technology Bureau(W20170003)

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摘要/Abstract

异香豆素是一种重要的药物分子, 目前已经开发了许多合成途径, 主要集中在苯甲酸或其他物质与炔烃的环化.亚磺酰基苯甲酰胺在螯合辅助的芳烃邻位C—H官能化中可以轻松地制备, 碳酸亚乙烯酯可以建立无氧化剂的催化体系, 使碳酸作为唯一的副产物. 在铑催化剂的存在下, 亚磺酰基苯甲酰胺和碳酸亚乙烯酯之间形成了环化, 通过导向基团辅助的邻位C—H偶联和分子内醇解, 以中等至良好的产率获得未取代的异香豆素.

关键词: 铑, 亚磺酰基苯甲酰胺, 碳酸亚乙烯酯

Isocoumarins are an important pharmaceutical compounds. Many synthetic pathways have been developed, mainly focusing on the cyclization of benzoic acid or other with alkynes. Sulfinylidene benzamides were facilely prepared and developed in the chelation-assisted arene ortho-C—H functionalization, and vinylene carbonate can establish an oxidant-free catalytic system, giving carbonic acid as a sole side product. In the presence of rhodium catalyst, an annulation between sulfinylidene benzamides and vinylene carbonate was developed, proceeding with directing group-assisted ortho-C—H coupling and intramolecular alcoholysis toward nonsubstituted isocoumarins in moderate to good yields.

Key words: rhodium, sulfinylidene benzamides, vinylene carbonate

引用此文

王璐, 邵莺, 陈帆, 钱鹏程, 成江. 铑催化定位基促进芳环C—H键和碳酸亚乙烯酯的缩合得到异香豆素[J]. 有机化学, 2022, 42(1): 242-248.

Lu Wang, Ying Shao, Fan Chen, Pengcheng Qian, Jiang Cheng. Rhodium-Catalyzed Directing Group-Assisted Annulation of Arene C—H Bond with Vinylene Carbonate toward Isocoumarins[J]. Chinese Journal of Organic Chemistry, 2022, 42(1): 242-248.

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Entry	Catalyst	Oxidant	Additive 1	Additive 2	Yield^b
1	Cp*Rh(OAc)₂•H₂O	AgSbF₆	Cu(OAc)₂•H₂O	—	<5%
2	[Cp*IrCl₂]₂	AgSbF₆	Cu(OAc)₂•H₂O	—	<5%
3	[Cp*RhCl₂]₂	AgSbF₆	Cu(OAc)₂•H₂O	—	15%
4	[Cp*RhCl₂]₂	AgSbF₆	—	—	NR
5	[Cp*RhCl₂]₂	AgBF₄	Cu(OAc)₂•H₂O	—	22%
6	[Cp*RhCl₂]₂	AgNTf₂	Cu(OAc)₂•H₂O	—	56%, 49%^c, 51%^d
7	[Cp*RhCl₂]₂	AgNTf₂	Cu(OTf)₂	—	39%
8	[Cp*RhCl₂]₂	AgNTf₂	CuI	—	45%
9	[Cp*RhCl₂]₂	AgNTf₂	Zn(OAc)₂•H₂O	—	<5%
10	[Cp*RhCl₂]₂	AgNTf₂	Zn(OTf)₂	—	58%
11	[Cp*RhCl₂]₂	AgNTf₂	Cu(OAc)₂•H₂O	HOAc	49%
12	[Cp*RhCl₂]₂	AgNTf₂	Cu(OAc)₂•H₂O	Zn(OTf)₂	78%, 71%^e, 64%^f
13	[Cp*RhCl₂]₂	AgNTf₂	Cu(OAc)₂•H₂O	ZnCl₂	54%, 65%^g, 20%^h
14	[Cp*RhCl₂]₂	AgNTf₂	Cu(OAc)₂•H₂O	Zn(OTf)₂	66%ⁱ
15	[Cp*RhCl₂]₂	AgNTf₂	Cu(OAc)₂•H₂O	Zn(OTf)₂	59%^j
16	[Cp*RhCl₂]₂	AgNTf₂	Cu(OAc)₂•H₂O	Zn(OTf)₂	62%^k

Entry	Catalyst	Oxidant	Additive 1	Additive 2	Yield^b
1	Cp*Rh(OAc)₂•H₂O	AgSbF₆	Cu(OAc)₂•H₂O	—	<5%
2	[Cp*IrCl₂]₂	AgSbF₆	Cu(OAc)₂•H₂O	—	<5%
3	[Cp*RhCl₂]₂	AgSbF₆	Cu(OAc)₂•H₂O	—	15%
4	[Cp*RhCl₂]₂	AgSbF₆	—	—	NR
5	[Cp*RhCl₂]₂	AgBF₄	Cu(OAc)₂•H₂O	—	22%
6	[Cp*RhCl₂]₂	AgNTf₂	Cu(OAc)₂•H₂O	—	56%, 49%^c, 51%^d
7	[Cp*RhCl₂]₂	AgNTf₂	Cu(OTf)₂	—	39%
8	[Cp*RhCl₂]₂	AgNTf₂	CuI	—	45%
9	[Cp*RhCl₂]₂	AgNTf₂	Zn(OAc)₂•H₂O	—	<5%
10	[Cp*RhCl₂]₂	AgNTf₂	Zn(OTf)₂	—	58%
11	[Cp*RhCl₂]₂	AgNTf₂	Cu(OAc)₂•H₂O	HOAc	49%
12	[Cp*RhCl₂]₂	AgNTf₂	Cu(OAc)₂•H₂O	Zn(OTf)₂	78%, 71%^e, 64%^f
13	[Cp*RhCl₂]₂	AgNTf₂	Cu(OAc)₂•H₂O	ZnCl₂	54%, 65%^g, 20%^h
14	[Cp*RhCl₂]₂	AgNTf₂	Cu(OAc)₂•H₂O	Zn(OTf)₂	66%ⁱ
15	[Cp*RhCl₂]₂	AgNTf₂	Cu(OAc)₂•H₂O	Zn(OTf)₂	59%^j
16	[Cp*RhCl₂]₂	AgNTf₂	Cu(OAc)₂•H₂O	Zn(OTf)₂	62%^k

铑催化定位基促进芳环C—H键和碳酸亚乙烯酯的缩合得到异香豆素

Rhodium-Catalyzed Directing Group-Assisted Annulation of Arene C—H Bond with Vinylene Carbonate toward Isocoumarins

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