Year: 2026
Type: preprint
Abstract: Dimethyl(phenyl)(2,3,3-trifluoroallyl)silane, the defluorosilylation product of HFO-1234yf, reacts with KHMDS to form 3,3-difluoro-1-dimethyl(phenyl)silylpropyne. The mechanism of this transformation was rationalized through DFT calculations. Deprotonation and subsequent β-fluoride elimination leads to an allene intermediate. A base-catalyzed 1,3-proton migration from the allene then results in the difluoromethylated alkyne product. This alkynyl silane can undergo transmetalation with NHC-ligated Group 11 transition metal chloride complexes to form novel metal acetylide compounds with a 3,3-difluoropropynyl motif.
Source: ChemRxiv
Institutions: Imperial College London, University of Edinburgh
Language: English
Subfield: Organic Chemistry
Field: Chemistry
Domain: Physical Sciences
Open Access status: green
OpenAlex ID: W7222450171