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Decarbonylative cycloaddition of 1H-indene-1,2,3-trione and norbornene via rhodium(I)-catalyzed carbon–carbon bond cleavage
New Journal of Chemistry ( IF 2.7 ) Pub Date : 2022-05-06 , DOI: 10.1039/d2nj01708c
Zhenzhu Hu 1 , Yuhang Wang 1 , Peng Ma 1 , Jianhui Wang 1, 2 , Guiyan Liu 3
Affiliation  

2,3-Dihydro-1H-inden-1-one derivatives were synthesized by a [5+2−2] decarbonylative cycloaddition of 1H-indene-1,2,3-trione and norbornene via rhodium(I) catalyzed direct carbon–carbon bond cleavage. A catalytic system combining [Rh(COD)Cl]2 (5.0 mol%) and rac-BINAP(10 mol%) ligand was optimal for these transformations. Various functional groups were tolerated under standard reaction conditions. Although the reactions in most of the cases showed no regioselectivity, some substrates with a –OMe, –CN, or strong electron-withdrawing –CF3 group at the 4-position displayed high regioselectivity.

中文翻译:

1H-茚-1,2,3-三酮和降冰片烯通过铑(I)催化的碳-碳键断裂脱羰环加成

2,3-Dihydro-1 H -inden-1-one 衍生物是由 1 H -indene-1,2,3-trione 和降冰片烯通过铑( I ) 直接催化的 [5+2−2] 脱羰环加成反应合成的碳-碳键断裂。结合 [Rh(COD)Cl] 2 (5.0 mol%) 和rac -BINAP(10 mol%) 配体的催化体系是这些转化的最佳选择。在标准反应条件下可以耐受各种官能团。尽管在大多数情况下反应没有显示出区域选择性,但一些在 4 位具有-OMe、-CN 或强吸电子-CF 3基团的底物显示出高区域选择性。
更新日期:2022-05-06
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