Unknown

Dataset Information

0

Selective Boryl-Anion Migration in a Vinyl sp2 -sp3 Diborane Induced by Soft Borane Lewis Acids.


ABSTRACT: An intramolecular 1,2-boryl-anion migration from boron to carbon has been achieved by selective activation of the ??system in [(vinyl)B2 Pin2 )]- using "soft" BR3 electrophiles (BR3 =BPh3 or 9-aryl-BBN). The soft character is key to ensure 1,2-migration proceeds instead of oxygen coordination/B-O activation. The BR3 -induced 1,2-boryl-anion migration represents a triple borylation of a vinyl Grignard reagent using only B2 Pin2 and BR3 and forms differentially protected 1,1,2-triborylated alkanes. Notably, by increasing the steric bulk at the ??position of the vinyl Grignard reagent used to activate B2 Pin2 , 1,2-boryl-anion migration can be suppressed in favor of intermolecular {BPin}- transfer to BPh3 , thus enabling simple access to unsymmetrical sp2 -sp3 diboranes.

SUBMITTER: Fasano V 

PROVIDER: S-EPMC6221116 | biostudies-literature | 2018 Oct

REPOSITORIES: biostudies-literature

altmetric image

Publications

Selective Boryl-Anion Migration in a Vinyl sp<sup>2</sup> -sp<sup>3</sup> Diborane Induced by Soft Borane Lewis Acids.

Fasano Valerio V   Cid Jessica J   Procter Richard J RJ   Ross Emily E   Ingleson Michael J MJ  

Angewandte Chemie (International ed. in English) 20180910 40


An intramolecular 1,2-boryl-anion migration from boron to carbon has been achieved by selective activation of the π system in [(vinyl)B<sub>2</sub> Pin<sub>2</sub> )]<sup>-</sup> using "soft" BR<sub>3</sub> electrophiles (BR<sub>3</sub> =BPh<sub>3</sub> or 9-aryl-BBN). The soft character is key to ensure 1,2-migration proceeds instead of oxygen coordination/B-O activation. The BR<sub>3</sub> -induced 1,2-boryl-anion migration represents a triple borylation of a vinyl Grignard reagent using only  ...[more]

Similar Datasets

| S-EPMC5385571 | biostudies-literature
| S-EPMC7337987 | biostudies-literature
| S-EPMC5369401 | biostudies-literature
| S-EPMC10660343 | biostudies-literature
| S-EPMC4183600 | biostudies-literature
| S-EPMC5737768 | biostudies-literature
| S-EPMC3658162 | biostudies-literature
| S-EPMC7894291 | biostudies-literature
| S-EPMC2841226 | biostudies-literature
| S-EPMC3352766 | biostudies-other