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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
Chinese Journal of Chemistry ( IF 5.5 ) Pub Date : 2023-10-02 , DOI: 10.1002/cjoc.202300509 Bin Li 1 , Mengmeng Xie 1 , Jingyu Li 1 , Nana Shen 1 , Xinying Zhang 1 , Xuesen Fan 1
Chinese Journal of Chemistry ( IF 5.5 ) Pub Date : 2023-10-02 , DOI: 10.1002/cjoc.202300509 Bin Li 1 , Mengmeng Xie 1 , Jingyu Li 1 , Nana Shen 1 , Xinying Zhang 1 , Xuesen Fan 1
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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.
中文翻译：
钴催化的可切换 [4 + 1] 和 [4 + 1 + 1] 芳香酰胺与 2-重氮-1H-茚-1,3(2H)-二酮的螺环化：获得螺茚-2,1'-异吲哚啉酮和螺异色满-3,1'-异吲哚啉酮
在此，我们报道了螺环茚-2,1'-异吲哚啉酮和螺异色满-3,1'-异吲哚啉酮的条件控制发散合成，通过钴催化的形式[4 + 1]和[4 + 1 + 1]螺环化芳香族酰胺与2-重氮-1H-茚-1,3(2H ) -二酮。当反应在空气下在乙酸乙酯中进行时，通过Co(II)催化的CH/NH [4 + 1]螺环化形成螺茚-2,1'-异二氢吲哚酮。另一方面，当反应在CH 3 CN中的O 2下进行时，通过用O对原位形成的螺环茚-2,1'-异二氢吲哚酮进行Baeyer-Villiger氧化，生成螺环异色满-3,1'-异二氢吲哚酮。2作为一种廉价且环保的氧源。总的来说，这些方案具有使用非贵重且储量丰富的金属催化剂、无需额外添加剂、高效和区域选择性等优点。克级合成和导向基团的去除进一步凸显了其实用性。
更新日期：2023-10-02
中文翻译：
钴催化的可切换 [4 + 1] 和 [4 + 1 + 1] 芳香酰胺与 2-重氮-1H-茚-1,3(2H)-二酮的螺环化：获得螺茚-2,1'-异吲哚啉酮和螺异色满-3,1'-异吲哚啉酮
在此，我们报道了螺环茚-2,1'-异吲哚啉酮和螺异色满-3,1'-异吲哚啉酮的条件控制发散合成，通过钴催化的形式[4 + 1]和[4 + 1 + 1]螺环化芳香族酰胺与2-重氮-1H-茚-1,3(2H ) -二酮。当反应在空气下在乙酸乙酯中进行时，通过Co(II)催化的CH/NH [4 + 1]螺环化形成螺茚-2,1'-异二氢吲哚酮。另一方面，当反应在CH 3 CN中的O 2下进行时，通过用O对原位形成的螺环茚-2,1'-异二氢吲哚酮进行Baeyer-Villiger氧化，生成螺环异色满-3,1'-异二氢吲哚酮。2作为一种廉价且环保的氧源。总的来说，这些方案具有使用非贵重且储量丰富的金属催化剂、无需额外添加剂、高效和区域选择性等优点。克级合成和导向基团的去除进一步凸显了其实用性。
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