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Structure-Modified Germatranes for Pd-Catalyzed Biaryl Synthesis

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journal contribution
posted on 04.09.2018, 00:00 authored by Hai-Jie Song, Wei-Tao Jiang, Qiao-Lan Zhou, Meng-Yu Xu, Bin Xiao
Germanium, a member of 14th group that falls between Si and Sn, has remained considerably ignored as a nucleophile for a long time. Compared with other forms of Ge-containing nucleophiles, germatranes are structure-defined, easily accessible, and stabilized nucleophilic fragments, but they fail to meet the need of high reactivity and facile introducing to organics. Herein, we report a modified structure of germatranes, whose cross-coupling reactivity is greatly improved. The structure can be easily constructed from inexpensive industrial GeO2, and corresponding Ge-Cl and Ge-H can also be obtained after facile transformations. Moreover, Ar-Ge can be effectively synthesized either from Grignard reagents or Pd-catalyzed germylation of aryl halides.