钯（II）催化的α-甲氧基酰胺与芳炔的C(sp)-H键活化/C-N键裂解环化反应
Palladium(II)-Catalyzed C(sp)-H Bond Activation/C-N Bond Cleavage Annulation of -Methoxy Amides and Arynes.
作者信息
Cheng Xiu-Fen, Yu Ting, Liu Yi, Wang Nan, Chen Zhenzhen, Zhang Guang-Lu, Tong Lili, Tang Bo
机构信息
College of Chemistry, Chemical Engineering and Materials Science, Collaborative Innovation Center of Functionalized Probes for Chemical Imaging in Universities of Shandong, Key Laboratory of Molecular and Nano Probes, Ministry of Education, Shandong Provincial Key Laboratory of Clean Production of Fine Chemicals, Shandong Normal University, Jinan 250014, P. R. China.
出版信息
Org Lett. 2022 Mar 25;24(11):2087-2092. doi: 10.1021/acs.orglett.2c00161. Epub 2022 Mar 14.
The Pd(II)-catalyzed C-H bond activation/C-N bond cleavage annulation reaction of -alkyoxyamide aryne is developed to synthesize 9,10-dihydrophenanthrenone derivatives. This reaction exhibited good functional group compatibility with yields up to 92%. Detailed mechanistic studies showed that the key to C-N bond cleavage is the formed eight-membered palladacycle intermediate undergoing nucleophilic addition to the carbonyl group, which provides a new and practical way for -alkoxyamide directed C-H bond activation.
开发了钯（II）催化的α-烷氧基酰胺芳炔的C-H键活化/C-N键裂解环化反应，以合成9,10-二氢菲醌衍生物。该反应表现出良好的官能团兼容性，产率高达92%。详细的机理研究表明，C-N键裂解的关键是形成的八元钯环中间体对羰基进行亲核加成，这为α-烷氧基酰胺导向的C-H键活化提供了一种新的实用方法。
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