Dichlorophenylborane

Chemical Properties

clear colorless liquid

History

In 1880, Michaelis and co-workers began to investigate aryl-boranes to determine the valency of boron which was, at thetime, debated to be three or five. They reacted gaseous BCl3with diphenylmercury at elevated temperatures in a sealedtube and observed the formation of dichlorophenylborane and HgCl2. Dichlorophenylborane was isolated via distillationand was characterized by elemental analysis and conclusivefollow-up chemistry[1].

Uses

Catalyst for:

• Antiproliferative macrolide and cell migration inhibitor lactimidomycin
• Enantioselective synthesis of polyketide segments using vinylogous Mukaiyama aldol reactions
• Enantioselective Diels-Alder cycloadditions after its reaction with allo-threonine derivatives
• Stereoselective alkylative ring opening of cyclic anhydrides
• Cross-metathesis reaction of amino derivatives with olefins
• Asymmetric acetate aldol reactions
• The reaction of aryl aldehydes with styrene and (E)-β-methylstyrene

Uses

Dichlorophenylborane is widely used as a catalyst in Antiproliferative macrolide and cell migration inhibitor lactimidomycin and in enantioselective synthesis of polypeptide segments using vinylogous Mukaiyama aldol reactions and in enantioselective Diels-Alder cycloadditions after its reaction with allo-threonine derivatives. It is a stereo selective alkylative ring opening of cyclic anhydrides and in cross-metathesis reaction of amino derivatives with olefines.

References

[1] Sarina M. Berger, Prof.?Dr. Todd B. Marder, Matthias Ferger. “Synthetic Approaches to Triarylboranes from 1885 to 2020.” Chemistry - A European Journal 27 24 (2021): 7043–7058.