Cobalt-Catalyzed Switchable [4 + 1] and [4 + 1 + 1] Spirocyclization of Aromatic Amides with 2-Diazo-1H-indene-1,3(2H)-dione: Access to Spiro Indene-2,1'-isoindolinones and Spiro Isochroman-3,1'-isoindolinones
Corresponding Author
Bin Li
State Key Laboratory of Antiviral Drugs, Pingyuan Laboratory, Key Laboratory of Green Chemical Media and Reactions, Key Laboratory for Yellow River and Huai River Water Environmental Pollution Control, Ministry of Education, School of Environment, School of Chemistry and Chemical Engineering, Henan Normal University, Xinxiang, Henan, 453007 China
E-mail: [email protected]; [email protected]Search for more papers by this authorMengmeng Xie
State Key Laboratory of Antiviral Drugs, Pingyuan Laboratory, Key Laboratory of Green Chemical Media and Reactions, Key Laboratory for Yellow River and Huai River Water Environmental Pollution Control, Ministry of Education, School of Environment, School of Chemistry and Chemical Engineering, Henan Normal University, Xinxiang, Henan, 453007 China
Search for more papers by this authorJingyu Li
State Key Laboratory of Antiviral Drugs, Pingyuan Laboratory, Key Laboratory of Green Chemical Media and Reactions, Key Laboratory for Yellow River and Huai River Water Environmental Pollution Control, Ministry of Education, School of Environment, School of Chemistry and Chemical Engineering, Henan Normal University, Xinxiang, Henan, 453007 China
Search for more papers by this authorNana Shen
State Key Laboratory of Antiviral Drugs, Pingyuan Laboratory, Key Laboratory of Green Chemical Media and Reactions, Key Laboratory for Yellow River and Huai River Water Environmental Pollution Control, Ministry of Education, School of Environment, School of Chemistry and Chemical Engineering, Henan Normal University, Xinxiang, Henan, 453007 China
Search for more papers by this authorXinying Zhang
State Key Laboratory of Antiviral Drugs, Pingyuan Laboratory, Key Laboratory of Green Chemical Media and Reactions, Key Laboratory for Yellow River and Huai River Water Environmental Pollution Control, Ministry of Education, School of Environment, School of Chemistry and Chemical Engineering, Henan Normal University, Xinxiang, Henan, 453007 China
Search for more papers by this authorCorresponding Author
Xuesen Fan
State Key Laboratory of Antiviral Drugs, Pingyuan Laboratory, Key Laboratory of Green Chemical Media and Reactions, Key Laboratory for Yellow River and Huai River Water Environmental Pollution Control, Ministry of Education, School of Environment, School of Chemistry and Chemical Engineering, Henan Normal University, Xinxiang, Henan, 453007 China
E-mail: [email protected]; [email protected]Search for more papers by this authorCorresponding Author
Bin Li
State Key Laboratory of Antiviral Drugs, Pingyuan Laboratory, Key Laboratory of Green Chemical Media and Reactions, Key Laboratory for Yellow River and Huai River Water Environmental Pollution Control, Ministry of Education, School of Environment, School of Chemistry and Chemical Engineering, Henan Normal University, Xinxiang, Henan, 453007 China
E-mail: [email protected]; [email protected]Search for more papers by this authorMengmeng Xie
State Key Laboratory of Antiviral Drugs, Pingyuan Laboratory, Key Laboratory of Green Chemical Media and Reactions, Key Laboratory for Yellow River and Huai River Water Environmental Pollution Control, Ministry of Education, School of Environment, School of Chemistry and Chemical Engineering, Henan Normal University, Xinxiang, Henan, 453007 China
Search for more papers by this authorJingyu Li
State Key Laboratory of Antiviral Drugs, Pingyuan Laboratory, Key Laboratory of Green Chemical Media and Reactions, Key Laboratory for Yellow River and Huai River Water Environmental Pollution Control, Ministry of Education, School of Environment, School of Chemistry and Chemical Engineering, Henan Normal University, Xinxiang, Henan, 453007 China
Search for more papers by this authorNana Shen
State Key Laboratory of Antiviral Drugs, Pingyuan Laboratory, Key Laboratory of Green Chemical Media and Reactions, Key Laboratory for Yellow River and Huai River Water Environmental Pollution Control, Ministry of Education, School of Environment, School of Chemistry and Chemical Engineering, Henan Normal University, Xinxiang, Henan, 453007 China
Search for more papers by this authorXinying Zhang
State Key Laboratory of Antiviral Drugs, Pingyuan Laboratory, Key Laboratory of Green Chemical Media and Reactions, Key Laboratory for Yellow River and Huai River Water Environmental Pollution Control, Ministry of Education, School of Environment, School of Chemistry and Chemical Engineering, Henan Normal University, Xinxiang, Henan, 453007 China
Search for more papers by this authorCorresponding Author
Xuesen Fan
State Key Laboratory of Antiviral Drugs, Pingyuan Laboratory, Key Laboratory of Green Chemical Media and Reactions, Key Laboratory for Yellow River and Huai River Water Environmental Pollution Control, Ministry of Education, School of Environment, School of Chemistry and Chemical Engineering, Henan Normal University, Xinxiang, Henan, 453007 China
E-mail: [email protected]; [email protected]Search for more papers by this authorComprehensive Summary
Herein, we report a condition-controlled divergent synthesis of spiro indene-2,1'-isoindolinones and spiro isochroman-3,1'-isoindolinones through cobalt-catalyzed formal [4 + 1] and [4 + 1 + 1] spirocyclization of aromatic amides with 2-diazo-1H-indene-1,3(2H)- dione. When the reaction is carried out under air in ethyl acetate, spiro indene-2,1'-isoindolinones are formed through Co(II)-catalyzed C—H/N—H [4 + 1] spirocyclization. When the reaction is run under O2 in CH3CN, on the other hand, spiro isochroman-3,1'-isoindolinones are generated through Baeyer-Villiger oxidation of the in situ formed spiro indene-2,1'-isoindolinones with O2 as a cheaper and environmental-friendly oxygen source. In general, these protocols have advantages such as using non-precious and earth-abundant metal catalyst, no extra additive, high efficiency and regioselectivity. A gram-scale synthesis and the removal of the directing group further highlight its utility.
Supporting Information
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Appendix S1: Supporting Information |
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