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].
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
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.
[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.
