首页|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 lsochroman-3,1'-isoindolinones

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 lsochroman-3,1'-isoindolinones

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Herein,we report a condition-controlled divergent synthesis of spiro indene-2,1'-isoindolinones and spiro isochroman-3,1'-isoindoli-nones 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)-cata-lyzed C—H/N—H[4+1]spirocyclization.When the reaction is run under O2 in CH3CN,on the other hand,spiro isochroman-3,1'-iso-indolinones 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.

Spiro indene-2,1'-isoindolinonesSpiro isochroman-3,1'-isoindolinones3d Transition metalsCobalt-catalyzedC—H ActivationSwitchable[4+1]and[4+1+1]spirocyclizationAromatic amides2-Diazo-1H-indene-1,3(2H)-dione

Bin Li、Mengmeng Xie、Jingyu Li、Nana Shen、Xinying Zhang、Xuesen Fan

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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

国家自然科学基金国家自然科学基金Central Plains Science and Technology Innovation Leader ProjectPostdoctoral Research Grant in Henan ProvinceHenan Key Laboratory of Organic Functional Molecules and Drug Innovation111 Project

22101075U2004189224200510009202103085D17007

2024

10.1002/cjoc.202300509

中国化学(英文版)
中国化学会 上海有机化学研究所

中国化学(英文版)

CSTPCD
影响因子：0.848
ISSN：1001-604X
年,卷(期)：2024.42(4)
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