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Chinese Journal of Organic Chemistry >

2018 , Vol. 38 >Issue 6: 1327 - 1340

DOI: https://doi.org/10.6023/cjoc201712044

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Experimental and Computational Research Progress on Cycloadditions of o-Carborane with Unsaturated Compounds

  • Mu Weihua ,
  • Cheng Ruijiao ,
  • Shang Yingwei ,
  • He Renze ,
  • Li Dongli ,
  • Fu Mian
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  • Faculty of Chemistry and Chemical Engineering, Yunnan Normal University, Kunming 650500

Received date: 2017-12-29

  Revised date: 2018-02-22

  Online published: 2018-02-28

Supported by

Project supported by the National Natural Science Foundation of China (Nos. 21763033, 21363028) and the Innovative Training Program for College Students in Yunnan Province.

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Abstract

o-Carboranes, as well as its derivative o-carborynes, can react with a variety of unsaturated compounds through cycloadditions and transform into various functionalized carboranes which have potential applications in many an area such as boron neutron capture therapy, catalytic systhesis and drug design. Recently, people have made remarkable achievements in the functionalization of o-carboranes and o-carborynes, especially in aspects of reaction condition optimization, selectivity controlling and reaction mechanism exploration. The most recent experimental achievements in the area of cycloaddition between o-carboranes and unsaturated compounds, alkenes, polycyclic or heterocyclic aromatics, in the past ten years are summarized. The reaction mechanisms and corresponding computational findings of o-carboryne-involved [2+2+2],[2+2+1],[2+2],[3+2],[4+2] and[5+2] cycloadditions are summarized and emphasized. Moreover, the prospects of future development in this area are discussed in the end.

Key words： boranes; carboranes; carborynes; cycloaddition; reaction mechanism; density functional theory

Cite this article

Mu Weihua , Cheng Ruijiao , Shang Yingwei , He Renze , Li Dongli , Fu Mian . Experimental and Computational Research Progress on Cycloadditions of o-Carborane with Unsaturated Compounds[J]. Chinese Journal of Organic Chemistry, 2018 , 38(6) : 1327 -1340 . DOI: 10.6023/cjoc201712044

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