3 years ago

Broad Scope [4 + 2] Cycloaddition of o-Carboryne with Pentafulvenes Using 1-Li-2-OTf-o-C2B10H10 as Precursor

Broad Scope [4 + 2] Cycloaddition of o-Carboryne with Pentafulvenes Using 1-Li-2-OTf-o-C2B10H10 as Precursor
Zaozao Qiu, Jie Zhang, Zuowei Xie
o-Carboryne (1,2-dehydro-o-carborane) generated in situ from 1-Li-2-OTf-o-C2B10H10 undergoes an efficient [4 + 2] cycloaddition with pentafulvenes at room temperature to give a series of carboranonorbornenes in good to high isolated yields. This reaction is compatible with many functional groups and has a very broad substrate scope from 6-mono- to 6,6′-disubstituted pentafulvenes and from alkyl to aryl substituents. Further transformations of the resultant [4 + 2] cycloaddition products have been carried out, affording various multifunctionalized o-carboranes.

Publisher URL: http://dx.doi.org/10.1021/acs.organomet.7b00574

DOI: 10.1021/acs.organomet.7b00574

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