铑催化2-芳基-2H-吲唑与硫叶立德的酰甲基化/串联环化反应高效构建6-芳基吲唑并[2,3-a]喹啉类衍生物

doi:10.6023/cjoc202206052

有机化学 ›› 2023, Vol. 43 ›› Issue (3): 1187-1196.DOI: 10.6023/cjoc202206052 上一篇下一篇

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研究论文

铑催化2-芳基-2H-吲唑与硫叶立德的酰甲基化/串联环化反应高效构建6-芳基吲唑并[2,3-a]喹啉类衍生物

汤振, 皮超^*(), 吴养洁, 崔秀灵^*()

郑州大学化学学院绿色催化研究中心河南省高校应用化学重点实验室河南省化学生物学与有机化学重点实验室郑州 450052

收稿日期:2022-06-28 修回日期:2022-08-25 发布日期:2022-09-15
通讯作者: 皮超, 崔秀灵
基金资助:
国家重点研发计划国际合作项目基金(2016YFE0132600); 河南省杰出外籍科学家工作室(GZS2020001); 河南省重点研发与推广专项(212102311068)

Rhodium-Catalyzed Tandem Acylmethylation/Annulation Reactions of 2-Aryl-2H-indazoles with Sulfoxonium Ylides: Easy Access to 6-Arylindazolo[2,3-a]quinolines

Zhen Tang, Chao Pi(), Yangjie Wu, Xiuling Cui()

Henan Key Laboratory of Chemical Biology and Organic Chemistry, Key Laboratory of Applied Chemistry of Henan Universities, Green Catalysis Center and College of Chemistry, Zhengzhou University, Zhengzhou 450052

Received:2022-06-28 Revised:2022-08-25 Published:2022-09-15
Contact: Chao Pi, Xiuling Cui
Supported by:
National Key R&D Program of China(2016YFE0132600); Henan Center for Outstanding Overseas Scientists(GZS2020001); Technological Project of Henan Province(212102311068)

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摘要/Abstract

报道了铑(III)催化2-芳基-2H-吲唑与硫叶立德的C—H键活化/环化反应, 有效地合成了6-芳基吲唑并[2,3-a]喹啉及其衍生物. 该反应效率高, 官能团兼容性好, 避免了外置氧化剂, 并且副产物仅为二甲基亚砜(DMSO)和水. 此外放大反应证明了该方式在工业上应用的可行性.

关键词: 2-芳基-2H-吲唑, 硫叶立德, 铑催化, 环化

An efficient synthesis of 6-arylindazolo[2,3-a]quinolines starting from 2-aryl-2H-indazoles with sulfoxonium ylides via rhodium(III)-catalyzed C—H activation and cyclization reaction has been described. This transformation features high efficiency, tolerates various functional groups, avoids external oxidant and produces dimethyl sulfoxide (DMSO) and H₂O as the sole by-products. In addition, the scale-up reaction demonstrated the practicability of this protocol in industry.

Key words: 2-aryl-2H-indazoles, sulfoxonium ylides, rhodium-catalyzed, cyclization

引用此文

汤振, 皮超, 吴养洁, 崔秀灵. 铑催化2-芳基-2H-吲唑与硫叶立德的酰甲基化/串联环化反应高效构建6-芳基吲唑并[2,3-a]喹啉类衍生物[J]. 有机化学, 2023, 43(3): 1187-1196.

Zhen Tang, Chao Pi, Yangjie Wu, Xiuling Cui. Rhodium-Catalyzed Tandem Acylmethylation/Annulation Reactions of 2-Aryl-2H-indazoles with Sulfoxonium Ylides: Easy Access to 6-Arylindazolo[2,3-a]quinolines[J]. Chinese Journal of Organic Chemistry, 2023, 43(3): 1187-1196.

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参考文献 14

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Entry	Variation from standard conditions	Yield^b/%
1	None	83
2	Without [Cp*RhCl₂]₂	NR
3	Without AgOTf	NR
4	CpCo(CO)I₂ instead of [CpRhCl₂]₂	NR
5	[CpIrCl₂]₂ instead of [CpRhCl₂]₂	NR
6	[RuCl₂(p-cymene)]₂ instead of [Cp*RhCl₂]₂	NR
7	Pd(OAc)₂ instead of [Cp*RhCl₂]₂	NR
8	AgSbF₆, AgNTf₂, PhCOOAg, Ag₂CO₃, CF₃COOAg, AgBF₄ instead of AgOTf	64/68/56/46/64/70
9	DCE, DCM, CH₃CN, THF, DMF, MeOH, HFIP, toluene instead of TFE	52/48/43/NR/NR/63/45/60
10	PivOH, HOAc, 1-AdCOOH, TsOH instead of PhCOOH	52/63/58/54
11	TFA (1 equiv.)	64
12	80 ℃ instead of 120 ℃	42

Entry	Variation from standard conditions	Yield^b/%
1	None	83
2	Without [Cp*RhCl₂]₂	NR
3	Without AgOTf	NR
4	CpCo(CO)I₂ instead of [CpRhCl₂]₂	NR
5	[CpIrCl₂]₂ instead of [CpRhCl₂]₂	NR
6	[RuCl₂(p-cymene)]₂ instead of [Cp*RhCl₂]₂	NR
7	Pd(OAc)₂ instead of [Cp*RhCl₂]₂	NR
8	AgSbF₆, AgNTf₂, PhCOOAg, Ag₂CO₃, CF₃COOAg, AgBF₄ instead of AgOTf	64/68/56/46/64/70
9	DCE, DCM, CH₃CN, THF, DMF, MeOH, HFIP, toluene instead of TFE	52/48/43/NR/NR/63/45/60
10	PivOH, HOAc, 1-AdCOOH, TsOH instead of PhCOOH	52/63/58/54
11	TFA (1 equiv.)	64
12	80 ℃ instead of 120 ℃	42

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铑催化2-芳基-2H-吲唑与硫叶立德的酰甲基化/串联环化反应高效构建6-芳基吲唑并[2,3-a]喹啉类衍生物

Rhodium-Catalyzed Tandem Acylmethylation/Annulation Reactions of 2-Aryl-2H-indazoles with Sulfoxonium Ylides: Easy Access to 6-Arylindazolo[2,3-a]quinolines

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