双铑(II)/Xantphos催化的C—H官能团化/烯丙基烷基化串联: 从N-芳基-α-重氮-β-酮酯简便制备3-酰基-3-烯丙基氧化吲哚衍生物

doi:10.6023/cjoc202206053

有机化学 ›› 2022, Vol. 42 ›› Issue (10): 3390-3397.DOI: 10.6023/cjoc202206053 上一篇下一篇

所属专题：不对称催化专辑

研究论文

双铑(II)/Xantphos催化的C—H官能团化/烯丙基烷基化串联: 从N-芳基-α-重氮-β-酮酯简便制备3-酰基-3-烯丙基氧化吲哚衍生物

李芳洁^a^,^b, 卢斌^b, 刘阳^a^,^*(), 王晓明^b^,^c^,^*()

a 肿瘤微环境响应药物研究湖南省重点实验室湖南省分子靶标新药研究南华大学衡阳医学院药学院协同创新中心湖南衡阳 421001
b 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分子合成科学卓越创新中心上海 200032
c 中国科学院大学杭州高等研究院化学与材料科学学院杭州 310024

收稿日期:2022-06-28 修回日期:2022-08-26 发布日期:2022-11-02
通讯作者: 刘阳, 王晓明
基金资助:
国家自然科学基金(21821002)

Dirhodium/Xantphos-Catalyzed Tandem C—H Functionalization/Allylic Alkylation: Direct Access to 3-Acyl-3-allyl Oxindole Derivatives from N-Aryl-α-diazo-β-keto Amides

Fangjie Li^a^,^b, Bin Lu^b, Yang Liu^a(), Xiaoming Wang^b^,^c()

a Hunan Provincial Key Laboratory of Tumor Microenvironment Responsive Drug Research, Hunan Province Cooperative Innovation Center for Molecular Target New Drug Study, School of Pharmacology, Hengyang Medical School, University of South China, Hengyang, Hunan 421001
b State Key Laboratory of Organometallic Chemistry, Center for Excellence in Molecular Synthesis, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032
c School of Chemistry and Materials Science, Hangzhou Institute for Advanced Study, University of Chinese Academy of Sciences, Hangzhou 310024

Received:2022-06-28 Revised:2022-08-26 Published:2022-11-02
Contact: Yang Liu, Xiaoming Wang
Supported by:
National Natural Science Foundation of China(21821002)

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摘要/Abstract

从易于获得的N-芳基-α-重氮-β-酮酰胺和烯丙基化合物出发, 利用新型的[Rh₂]/Xantphos催化体系一锅法合成了各种3-酰基-3-烯丙基的氧化吲哚衍生物. 这项工作的优点包括操作简便、反应条件温和、官能团兼容性良好和产物易于衍生化等. 初步的机理研究表明, 该反应可能经历卡宾诱导的C—H官能团化和Rh(II)/Xantphos催化的烯丙基烷基化串联过程. 此外, 选择Xantphos作为配体对于实现体系中的烯丙基烷基化过程至关重要.

关键词: 双铑络合物, 重氮化合物, 氧化吲哚, 季碳中心, 接力催化

A novel [Rh₂]/Xantphos-catalyzed one-pot sequence for the synthesis of diverse 3-acyl-3-allyl oxindole derivatives from easily available N-aryl-α-diazo-β-keto amides and allylic compounds has been developed. The notable features of this work include ease of operation, mild reaction conditions, good functional group compatibility and facile diversification of the products. Preliminary mechanistic studies indicate a tandem carbene-induced C—H functionalization and Rh(II)/Xantphos catalyzed allylic alkylation process. Moreover, the choice of Xantphos as the ligand is critical to enable the allylic alkylation process in this catalysis.

Key words: dirhodium(II), diazo compounds, oxindoles, quaternary centers, relay catalysis

引用此文

李芳洁, 卢斌, 刘阳, 王晓明. 双铑(II)/Xantphos催化的C—H官能团化/烯丙基烷基化串联: 从N-芳基-α-重氮-β-酮酯简便制备3-酰基-3-烯丙基氧化吲哚衍生物[J]. 有机化学, 2022, 42(10): 3390-3397.

Fangjie Li, Bin Lu, Yang Liu, Xiaoming Wang. Dirhodium/Xantphos-Catalyzed Tandem C—H Functionalization/Allylic Alkylation: Direct Access to 3-Acyl-3-allyl Oxindole Derivatives from N-Aryl-α-diazo-β-keto Amides[J]. Chinese Journal of Organic Chemistry, 2022, 42(10): 3390-3397.

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Entry	[Rh] cat.	Ligand	Base	Solvent	Yield^b/%
Entry	[Rh] cat.	Ligand	Base	Solvent	3a	4a
1	Rh₂(Oct)₄	Xantphos	Cs₂CO₃	DCE	—	51
2	Rh₂(Oct)₄	Xantphos	—	DCE	83	0
3	Rh₂(Oct)₄	Xantphos	KOAc	DCE	—	74
4	Rh₂(Oct)₄	Xantphos	KOAc	PhCF₃	—	88
5	Rh₂(OAc)₄	Xantphos	KOAc	PhCF₃	—	<1
6	Rh₂(TFA)₄	Xantphos	KOAc	PhCF₃	—	7
7	Rh(COD)₂BF₄	Xantphos	KOAc	PhCF₃	N.R.^c	N.R.^c
8	Rh₂(Oct)₄	BINAP	KOAc	PhCF₃	—	9
9	Rh₂(Oct)₄	dppb	KOAc	PhCF₃	—	7
10	Rh₂(Oct)₄	PPh₃	KOAc	PhCF₃	—	<5
11	Rh₂(Oct)₄	ⁱPr-NHC^d	KOAc	PhCF₃	—	<5
12^e	Rh₂(Oct)₄	Xantphos	KOAc	PhCF₃	—	83
13^f	Rh₂(Oct)₄	Xantphos	KOAc	PhCF₃	—	84
14	—	Xantphos	KOAc	PhCF₃	—	N.R.
15	Rh₂(Oct)₄	—	KOAc	PhCF₃	—	N.R.

Entry	[Rh] cat.	Ligand	Base	Solvent	Yield^b/%
Entry	[Rh] cat.	Ligand	Base	Solvent	3a	4a
1	Rh₂(Oct)₄	Xantphos	Cs₂CO₃	DCE	—	51
2	Rh₂(Oct)₄	Xantphos	—	DCE	83	0
3	Rh₂(Oct)₄	Xantphos	KOAc	DCE	—	74
4	Rh₂(Oct)₄	Xantphos	KOAc	PhCF₃	—	88
5	Rh₂(OAc)₄	Xantphos	KOAc	PhCF₃	—	<1
6	Rh₂(TFA)₄	Xantphos	KOAc	PhCF₃	—	7
7	Rh(COD)₂BF₄	Xantphos	KOAc	PhCF₃	N.R.^c	N.R.^c
8	Rh₂(Oct)₄	BINAP	KOAc	PhCF₃	—	9
9	Rh₂(Oct)₄	dppb	KOAc	PhCF₃	—	7
10	Rh₂(Oct)₄	PPh₃	KOAc	PhCF₃	—	<5
11	Rh₂(Oct)₄	ⁱPr-NHC^d	KOAc	PhCF₃	—	<5
12^e	Rh₂(Oct)₄	Xantphos	KOAc	PhCF₃	—	83
13^f	Rh₂(Oct)₄	Xantphos	KOAc	PhCF₃	—	84
14	—	Xantphos	KOAc	PhCF₃	—	N.R.
15	Rh₂(Oct)₄	—	KOAc	PhCF₃	—	N.R.

双铑(II)/Xantphos催化的C—H官能团化/烯丙基烷基化串联: 从N-芳基-α-重氮-β-酮酯简便制备3-酰基-3-烯丙基氧化吲哚衍生物

Dirhodium/Xantphos-Catalyzed Tandem C—H Functionalization/Allylic Alkylation: Direct Access to 3-Acyl-3-allyl Oxindole Derivatives from N-Aryl-α-diazo-β-keto Amides

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