Abstract
The insertion of the diazo derivative Me3SiCHN2 into pinB-SR σ bonds (R = Ph, Tol, Bn) allows a direct synthesis of multisubstituted H-C(SR)(Bpin)(SiMe3) compounds. Consecutive base-assisted transformations of HC(S)(B) (Si) systems lead to deborylative alkylations, Sommelet-Haüser rearrangements, and deprotoalkylations. Intramolecular cyclizations can be selectively performed either via desilylative or deborylative manifolds by fine-tuning the base employed.
Original language | English |
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Pages (from-to) | 3830-3833 |
Number of pages | 4 |
Journal | Organic Letters |
Volume | 18 |
Issue number | 15 |
DOIs | |
Publication status | Published - 5 Aug 2016 |
Externally published | Yes |
Keywords
- Addition-reactions
- Boronic esters
- Alkyl-halides
- Carbanions
- Deprotonation
- Homologation
- Diborylation
- Derivatives
- Alcohols
- Boranes