Journal
ORGANIC LETTERS
Volume 18, Issue 15, Pages 3830-3833Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.6b01840
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- Spanish Ministerio de Economia y Competitividad (MINECO) [CTQ2013-43395P]
- NSERC
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The insertion of the diazo derivative Me3SiCHN2 into pinB-SR sigma 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-Hauser rearrangements, and deprotoalkylations. Intramolecular cyclizations can be selectively performed either via desilylative or deborylative manifolds by fine-tuning the base employed.
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