Strategic Trimethylsilyldiazomethane Insertion into pinB-SR Followed by Selective Alkylations

Marc G. Civit, Jordi Royes, Christopher M. Vogels, Stephen A. Westcott, Ana B. Cuenca, Elena Fernández

Research output: Indexed journal article Articlepeer-review

17 Citations (Scopus)

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 languageEnglish
Pages (from-to)3830-3833
Number of pages4
JournalOrganic Letters
Volume18
Issue number15
DOIs
Publication statusPublished - 5 Aug 2016
Externally publishedYes

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