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

doi:10.6023/cjoc202106023

Chinese Journal of Organic Chemistry ›› 2022, Vol. 42 ›› Issue (1): 242-248.DOI: 10.6023/cjoc202106023 Previous Articles Next Articles

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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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Abstract

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

Cite this article

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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References 19

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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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