Rh(III)-Catalyzed [4+2] Annulation of Indoles with Sulfoxonium Ylides for the Synthesis of Dihydropyrimidoindolone Derivatives

doi:10.6023/cjoc202103027

Chinese Journal of Organic Chemistry ›› 2021, Vol. 41 ›› Issue (8): 3171-3179.DOI: 10.6023/cjoc202103027 Previous Articles Next Articles

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铑催化的吲哚与亚砜型叶立德的[4+2]环化反应构建二氢嘧啶并吲哚酮衍生物

舒赛^a, 黄志斌^a, 陈宇杰^a, 杨闪^a, 蒋雅琦琪^a, 张静宇^a^,^*(), 赵应声^a^,^b^,^*()

a 苏州大学材料与化学化工学部江苏苏州 215123
b 河南师范大学化学化工学院河南新乡 453000

收稿日期:2021-03-16 修回日期:2021-04-10 发布日期:2021-05-14
通讯作者: 张静宇, 赵应声
基金资助:
国家自然科学基金(21772139); 国家自然科学基金(21572149); 江苏省高等学校自然科学基金重大基础研究(15KJA150006); 江苏省高等学校自然科学基金重大基础研究(17KJA150006); 江苏省杰出青年自然科学基金(BK2018g0041); 苏州科技基础设施项目(SZS2018201708); 河南师范大学化学骨干特色学科开放基金; 江苏高校优势学科建设工程资助项目

Rh(III)-Catalyzed [4+2] Annulation of Indoles with Sulfoxonium Ylides for the Synthesis of Dihydropyrimidoindolone Derivatives

Sai Shu^a, Zhibin Huang^a, Yujie Chen^a, Shan Yang^a, Yaqiqi Jiang^a, jingyu Zhang^a(), Yingsheng Zhao^a^,^b()

a College of Chemistry, Chemical Engineering and Materials Science, Soochow University, Suzhou, Jiangsu 215123
b School of Chemistry and Chemical Engineering, Henan Normal University, Xinxiang, Henan 453000

Received:2021-03-16 Revised:2021-04-10 Published:2021-05-14
Contact: jingyu Zhang, Yingsheng Zhao
Supported by:
National Natural Science Foundation of China(21772139); National Natural Science Foundation of China(21572149); Major Basic Research Project of the Natural Science Foundation of Jiangsu Higher Education Institutions(15KJA150006); Natural Science Found for Distinguished Young Scholars of Jiangsu Province(BK2018g0041); Project of Scientific and Technologic infrastructure of Suzhou(SZS2018201708); Open Foundation of Backbone Characteristic Discipline of Chemistry of Henan Normal University; Priority Academic Program Development of Jiangsu Higher Education Institutions

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Sai Shu, Zhibin Huang, Yujie Chen, Shan Yang, Yaqiqi Jiang, jingyu Zhang, Yingsheng Zhao. Rh(III)-Catalyzed [4+2] Annulation of Indoles with Sulfoxonium Ylides for the Synthesis of Dihydropyrimidoindolone Derivatives[J]. Chinese Journal of Organic Chemistry, 2021, 41(8): 3171-3179.

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Entry	Catalyst	Additive (equiv.)	Solvent	Yield^b/% of 3a	Yield^b/% of 5
1	[Cp*IrCl₂]₂	AgSbF₆ (0.1)	DCE	17	trace
2	[RuCl₂(p-cymene)]₂	AgSbF₆ (0.1)	DCE	0	0
3	[Cp*RhCl₂]₂	AgSbF₆ (0.1)	DCE	30	23
4	[Cp*RhCl₂]₂	NaOAc (2)	DCE	37	32
5	[Cp*RhCl₂]₂	CsOAc (2)	DCE	38	29
6	[Cp*RhCl₂]₂	HOAc (1)	DCE	46	24
7	[Cp*RhCl₂]₂	PivOH (1)	DCE	67	9
8	[Cp*RhCl₂]₂	PivOH (1)	MeCN	60	<5
9	[Cp*RhCl₂]₂	PivOH (1)	THF	78	<5
10	[Cp*RhCl₂]₂	PivOH (1)	MeOH	54	13
11	[Cp*RhCl₂]₂	PivOH (1)	tBuOH	57	10
12^c	[Cp*RhCl₂]₂	PivOH (1)	THF	0	0
13^d	[Cp*RhCl₂]₂	PivOH (1)	THF	0	0
14^e	[Cp*RhCl₂]₂	PivOH (1)	THF	0	0
15^f	[Cp*RhCl₂]₂	PivOH (1)	THF	0	0
16^g	[Cp*RhCl₂]₂	PivOH (1)	THF	51	<5
17	—	PivOH (1)	THF	0	0
18	[Cp*RhCl₂]₂	—	THF	16	0

Entry	Catalyst	Additive (equiv.)	Solvent	Yield^b/% of 3a	Yield^b/% of 5
1	[Cp*IrCl₂]₂	AgSbF₆ (0.1)	DCE	17	trace
2	[RuCl₂(p-cymene)]₂	AgSbF₆ (0.1)	DCE	0	0
3	[Cp*RhCl₂]₂	AgSbF₆ (0.1)	DCE	30	23
4	[Cp*RhCl₂]₂	NaOAc (2)	DCE	37	32
5	[Cp*RhCl₂]₂	CsOAc (2)	DCE	38	29
6	[Cp*RhCl₂]₂	HOAc (1)	DCE	46	24
7	[Cp*RhCl₂]₂	PivOH (1)	DCE	67	9
8	[Cp*RhCl₂]₂	PivOH (1)	MeCN	60	<5
9	[Cp*RhCl₂]₂	PivOH (1)	THF	78	<5
10	[Cp*RhCl₂]₂	PivOH (1)	MeOH	54	13
11	[Cp*RhCl₂]₂	PivOH (1)	tBuOH	57	10
12^c	[Cp*RhCl₂]₂	PivOH (1)	THF	0	0
13^d	[Cp*RhCl₂]₂	PivOH (1)	THF	0	0
14^e	[Cp*RhCl₂]₂	PivOH (1)	THF	0	0
15^f	[Cp*RhCl₂]₂	PivOH (1)	THF	0	0
16^g	[Cp*RhCl₂]₂	PivOH (1)	THF	51	<5
17	—	PivOH (1)	THF	0	0
18	[Cp*RhCl₂]₂	—	THF	16	0

铑催化的吲哚与亚砜型叶立德的[4+2]环化反应构建二氢嘧啶并吲哚酮衍生物

Rh(III)-Catalyzed [4+2] Annulation of Indoles with Sulfoxonium Ylides for the Synthesis of Dihydropyrimidoindolone Derivatives

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