Synthesis of Esterified/Fused Isocoumarins via Rh-Catalyzed C—H Activation/Transannulative Coupling/Annulation of Phthalic Anhydrides with Cyclic 2-Diazo-1,3-diketones and Methanol

doi:10.6023/cjoc202205039

Chinese Journal of Organic Chemistry ›› 2022, Vol. 42 ›› Issue (11): 3816-3823.DOI: 10.6023/cjoc202205039 Previous Articles Next Articles

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铑催化的邻苯二甲酸酐与环状2-重氮-1,3-二酮和甲醇的串联C—H活化/跨环偶联/环化反应合成酯基官能化的并环异香豆素类化合物的研究

商铭洲^a, 张兰兰^b, 陈淼淼^b, 胡汪成^b, 何心伟^b^,^*(), 陆红健^a

^a南京大学化学化工学院南京 210093
^b安徽师范大学化学与材料科学学院安徽芜湖 241002

收稿日期:2022-05-22 修回日期:2022-07-03 发布日期:2022-07-13
通讯作者: 何心伟
基金资助:
国家自然科学基金(21772001); 国家自然科学基金(22071100); 大学生创新创业训练计划(202110370035)

Synthesis of Esterified/Fused Isocoumarins via Rh-Catalyzed C—H Activation/Transannulative Coupling/Annulation of Phthalic Anhydrides with Cyclic 2-Diazo-1,3-diketones and Methanol

Mingzhou Shang^a, Lanlan Zhang^b, Miaomiao Chen^b, Wangcheng Hu^b, Xinwei He^b(), Hongjian Lu^a

^aSchool of Chemistry and Chemical Engineering, Nanjing University, Nanjing 210093
^bCollege of Chemistry and Materials Science, Anhui Normal University, Wuhu, Anhui 241000

Received:2022-05-22 Revised:2022-07-03 Published:2022-07-13
Contact: Xinwei He
Supported by:
National Natural Science Foundation of China(21772001); National Natural Science Foundation of China(22071100); National Undergraduate Training Program for Innovation and Entrepreneurship(202110370035)

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Abstract

A rhodium(III)-catalyzed cascade reaction of phthalic anhydrides with cyclic 2-diazo-1,3-diketones and methanol for modular access to esterified cyclohexenone-fused isocoumarins has been developed. This strategy involves the process of one C—C and two C—O bonds formation through C—H activation, transannulative coupling and subsequent annulation process. Furthermore, no additive and base are needed in this transformation, and interestingly, the reaction could proceed well under air atmosphere with broad substrate and good functional groups tolerance.

Key words: annulation, C—H activation, diazo compound, isocoumarin, phthalic anhydride

Cite this article

Mingzhou Shang, Lanlan Zhang, Miaomiao Chen, Wangcheng Hu, Xinwei He, Hongjian Lu. Synthesis of Esterified/Fused Isocoumarins via Rh-Catalyzed C—H Activation/Transannulative Coupling/Annulation of Phthalic Anhydrides with Cyclic 2-Diazo-1,3-diketones and Methanol[J]. Chinese Journal of Organic Chemistry, 2022, 42(11): 3816-3823.

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Fig. & Tab. 6

References 21

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Entry	Catalyst	Solvent	Temp./℃	Time/h	Yield^b/%
1	Rh₂(OAc)₄	MeOH	Reflux	15	Trace
2	Rh₂(oct)₄	MeOH	Reflux	15	Trace
3	(PPh₃)₃RuCl₂	MeOH	Reflux	15	Trace
4	[(p-cymene)RuCl₂]₂	MeOH	Reflux	15	51
5	[Cp*RhCl₂]₂	MeOH	Reflux	15	83
6	Ni(COD)₂	MeOH	Reflux	15	nr
7	Ni(PPh₃)₂Cl₂	MeOH	Reflux	15	nr
8	Ni(OTf)₂	MeOH	Reflux	15	nr
9^c	[Cp*RhCl₂]₂	MeOH	Reflux	15	60
10^d	[Cp*RhCl₂]₂	MeOH	Reflux	15	62
11^e	[Cp*RhCl₂]₂	MeOH	Reflux	15	71
12^f	[Cp*RhCl₂]₂	MeOH	Reflux	15	83
13	—	MeOH	Reflux	15	nr
14	[Cp*RhCl₂]₂	DMF	Reflux	15	Trace
15	[Cp*RhCl₂]₂	DCM	Reflux	15	35
16	[Cp*RhCl₂]₂	MeCN	Reflux	15	Trace
17	[Cp*RhCl₂]₂	THF	Reflux	15	54
18	[Cp*RhCl₂]₂	Toluene	Reflux	15	Trace
19	[Cp*RhCl₂]₂	1,4-Dioxane	Reflux	15	Trace
20	[Cp*RhCl₂]₂	MeOH	25	15	20
21	[Cp*RhCl₂]₂	MeOH	50	15	45
22	[Cp*RhCl₂]₂	MeOH	Reflux	1	15
23	[Cp*RhCl₂]₂	MeOH	Reflux	5	20
24	[Cp*RhCl₂]₂	MeOH	Reflux	10	76
25	[Cp*RhCl₂]₂	MeOH	Reflux	20	83

Entry	Catalyst	Solvent	Temp./℃	Time/h	Yield^b/%
1	Rh₂(OAc)₄	MeOH	Reflux	15	Trace
2	Rh₂(oct)₄	MeOH	Reflux	15	Trace
3	(PPh₃)₃RuCl₂	MeOH	Reflux	15	Trace
4	[(p-cymene)RuCl₂]₂	MeOH	Reflux	15	51
5	[Cp*RhCl₂]₂	MeOH	Reflux	15	83
6	Ni(COD)₂	MeOH	Reflux	15	nr
7	Ni(PPh₃)₂Cl₂	MeOH	Reflux	15	nr
8	Ni(OTf)₂	MeOH	Reflux	15	nr
9^c	[Cp*RhCl₂]₂	MeOH	Reflux	15	60
10^d	[Cp*RhCl₂]₂	MeOH	Reflux	15	62
11^e	[Cp*RhCl₂]₂	MeOH	Reflux	15	71
12^f	[Cp*RhCl₂]₂	MeOH	Reflux	15	83
13	—	MeOH	Reflux	15	nr
14	[Cp*RhCl₂]₂	DMF	Reflux	15	Trace
15	[Cp*RhCl₂]₂	DCM	Reflux	15	35
16	[Cp*RhCl₂]₂	MeCN	Reflux	15	Trace
17	[Cp*RhCl₂]₂	THF	Reflux	15	54
18	[Cp*RhCl₂]₂	Toluene	Reflux	15	Trace
19	[Cp*RhCl₂]₂	1,4-Dioxane	Reflux	15	Trace
20	[Cp*RhCl₂]₂	MeOH	25	15	20
21	[Cp*RhCl₂]₂	MeOH	50	15	45
22	[Cp*RhCl₂]₂	MeOH	Reflux	1	15
23	[Cp*RhCl₂]₂	MeOH	Reflux	5	20
24	[Cp*RhCl₂]₂	MeOH	Reflux	10	76
25	[Cp*RhCl₂]₂	MeOH	Reflux	20	83

铑催化的邻苯二甲酸酐与环状2-重氮-1,3-二酮和甲醇的串联C—H活化/跨环偶联/环化反应合成酯基官能化的并环异香豆素类化合物的研究

Synthesis of Esterified/Fused Isocoumarins via Rh-Catalyzed C—H Activation/Transannulative Coupling/Annulation of Phthalic Anhydrides with Cyclic 2-Diazo-1,3-diketones and Methanol

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