4.6 Article

RhIII-Catalyzed Functionalization of closo-Dodecaborates by Selective B-H Activation: Bypassing Competitive C-H Activation

期刊

CHEMISTRY-A EUROPEAN JOURNAL
卷 24, 期 59, 页码 15812-15817

出版社

WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201803455

关键词

alkenylation; alkylation; B-H activation; boron clusters; cage compounds; rhodium catalysis

资金

  1. Natural Science Foundation of China [21472166]
  2. National Basic Research Program of China (973 project) [2015CB856500]
  3. Chinese 1000 Young Talents Plan

向作者/读者索取更多资源

The closo-dodecaborate dianion is a fundamental icosahedral boron cage with 12 identical B-H vertices. The chemistry and applications of boron clusters have inspired researchers ever since their discovery several decades ago, and the selective modification of the cage positions has remained a major synthetic challenge. A rhodium(III)-catalyzed B-H functionalization-cyclization cascade of closo-dodecaborate amides is reported. The transformations occur chemoselectively at B-H positions in the presence of C-H bonds prone to competitive cyclometalation. Previously inaccessible cage derivatives with B-C(sp(2)) and B-C(sp(3)) bonds as well as a fused diboraoxazole ring are obtained in a one-pot process. The reactions proceed under mild conditions and exhibit complete cage regioselectivity with broad functional group tolerance. These cluster derivatives enable a largely extended investigation of the application of anionic boron clusters in research areas such as photoluminescent materials and medicinal chemistry.

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