Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 56, Issue 44, Pages 13747-13751Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201707914
Keywords
density-functional calculations; electron transfer; hydrides; reaction mechanisms; silicon
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Funding
- University of Strathclyde
- GSK
- EPSRC [EP/K000586/1, EP/N509371/1]
- SFC
- WestCHEM
- EPSRC [1688241] Funding Source: UKRI
- Engineering and Physical Sciences Research Council [1688241] Funding Source: researchfish
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Recent studies by Stoltz, Grubbs et al. have shown that triethylsilane and potassium tert-butoxide react to form a highly attractive and versatile system that shows (reversible) silylation of arenes and heteroarenes as well as reductive cleavage of C-O bonds in aryl ethers and C-S bonds in aryl thioethers. Their extensive mechanistic studies indicate a complex network of reactions with a number of possible intermediates and mechanisms, but their reactions likely feature silyl radicals undergoing addition reactions and S(H)2 reactions. This paper focuses on the same system, but through computational and experimental studies, reports complementary facets of its chemistry based on a) single-electron transfer (SET), and b) hydride delivery reactions to arenes.
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