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Updated: Sep 30, 2026

Preparation of a Corannulene-functionalized Hexahelicene by Copper(I)-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units
Published on: September 18, 2016
Copper(I)-Catalyzed Asymmetric Hydrogermylation of 3,3-Disubstituted Cyclopropenes
Jia-Heng Li1, Qing-Yi Ru1, Hu Tian1
1State Key Laboratory of Fluorine and Nitrogen Chemistry and Advanced Materials, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences, Shanghai, China.
Abstract:
Catalytic asymmetric approaches to enantioenriched organogermanium compounds remain severely underdeveloped. Herein, we report a CuOAc-catalyzed enantioselective hydrogermylation of 3,3-disubstituted cyclopropenes, which furnishes structurally diverse chiral organogermanes in high to excellent diastereo- and enantioselectivities. Control experiments demonstrate that copper carboxylate is uniquely effective for this transformation. In contrast, catalytic systems composed of Cu(CH3CN)4PF6 and an exogenous base (e.g., triethylamine, Barton's base) afford negligible reactivity. Mechanistic studies elucidate that the CuOAc-bisphosphine catalysts enable the critical deprotonation of H3GeAr/H2GeAr2 through a possible synergistic six-membered cyclic transition state. Finally, versatile post-functionalization of the obtained products further expands the structural library of enantioenriched organogermanium compounds.
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