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Lewis Acid Catalyzed Transfer Hydromethallylation for the Construction of Quaternary Carbon Centers.
- Source :
-
Angewandte Chemie (International ed. in English) [Angew Chem Int Ed Engl] 2019 Oct 21; Vol. 58 (43), pp. 15386-15389. Date of Electronic Publication: 2019 Sep 12. - Publication Year :
- 2019
-
Abstract
- The design and gram-scale synthesis of a cyclohexa-1,4-diene-based surrogate of isobutene gas is reported. Using the highly electron-deficient Lewis acid B(C <subscript>6</subscript> F <subscript>5</subscript> ) <subscript>3</subscript> , application of this surrogate in the hydromethallylation of electron-rich styrene derivatives provided sterically congested quaternary carbon centers. The reaction proceeds by C(sp <superscript>3</superscript> )-C(sp <superscript>3</superscript> ) bond formation at a tertiary carbenium ion that is generated by alkene protonation. The possibility of two concurrent mechanisms is proposed on the basis of mechanistic experiments using a deuterated surrogate.<br /> (© 2019 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA.)
Details
- Language :
- English
- ISSN :
- 1521-3773
- Volume :
- 58
- Issue :
- 43
- Database :
- MEDLINE
- Journal :
- Angewandte Chemie (International ed. in English)
- Publication Type :
- Academic Journal
- Accession number :
- 31449730
- Full Text :
- https://doi.org/10.1002/anie.201909852