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 aromat...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.展开更多
Geminal bis(silanes) are unique orga no sila ne species containing one sp^3-carbon attached with two silyl groups, which have emerged as attractive synthetic building blocks.[1] In spite of the usefulness, the scarcit...Geminal bis(silanes) are unique orga no sila ne species containing one sp^3-carbon attached with two silyl groups, which have emerged as attractive synthetic building blocks.[1] In spite of the usefulness, the scarcity of synthetic methods to approach gem-bis(silanes) extremely restricts their potentialities for broader applications.展开更多
基金the National Natural Science Foundation of China(22101075,U2004189)Central Plains Science and Technology Innovation Leader Project(224200510009)+1 种基金Postdoctoral Research Grant in Henan Province(202103085)Henan Key Laboratory of Organic Functional Molecules and Drug Innovation,and 111 Project(D17007)for financial support.
文摘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.
基金Project supported by the National Natural Science Foundation of China(No.21772171)the National Basic Research Program of China(973 Program,No.2015CB856600)+1 种基金the Zhejiang Provincial Natural Science Foundation(No.LR19B020001)the K.P.Chao’s High Technology Development Foundation of Zhejiang University and the Fundamental Research Funds for the Central Universities~~
文摘Geminal bis(silanes) are unique orga no sila ne species containing one sp^3-carbon attached with two silyl groups, which have emerged as attractive synthetic building blocks.[1] In spite of the usefulness, the scarcity of synthetic methods to approach gem-bis(silanes) extremely restricts their potentialities for broader applications.
