O’Connor, Thomas J.; Mai, Binh Khanh; Nafie, Jordan; Liu, Peng; Toste, F. Dean published their research in Journal of the American Chemical Society in 2021. The article was titled 《Generation of Axially Chiral Fluoroallenes through a Copper-Catalyzed Enantioselective β-Fluoride Elimination》.Recommanded Product: 1-Bromo-3,4,5-trimethoxybenzene The article contains the following contents:
Herein we report the copper-catalyzed silylation of propargylic difluorides to generate axially chiral, tetrasubstituted monofluoroallenes in both good yields (27 examples >80%) and enantioselectivities (82-98% ee). Compared to previously reported synthetic routes to axially chiral allenes (ACAs) from prochiral substrates, a mechanistically distinct reaction has been developed: the enantiodiscrimination between enantiotopic fluorides to set an axial stereocenter. DFT calculations and vibrational CD (VCD) suggest that β-fluoride elimination from an alkenyl copper intermediate likely proceeds through a syn-β-fluoride elimination pathway rather than an anti-elimination pathway. The effects of the C1-sym. Josiphos-derived ligand on reactivity and enantioselectivity were investigated. Not only does this report showcase that alkenyl copper species (like their alkyl counterparts) can undergo β-fluoride elimination, but this elimination can be achieved in an enantioselective fashion. The results came from multiple reactions, including the reaction of 1-Bromo-3,4,5-trimethoxybenzene(cas: 2675-79-8Recommanded Product: 1-Bromo-3,4,5-trimethoxybenzene)
1-Bromo-3,4,5-trimethoxybenzene(cas: 2675-79-8) is an important raw material and intermediate used in organic synthesis, pharmaceuticals, agrochemicals and dyestuff.Recommanded Product: 1-Bromo-3,4,5-trimethoxybenzene1-Bromo-3,4,5-trimethoxybenzene can be used to synthesize symmetric 3,3′,4,4′,5,5′-hexamethoxydiphenylacetylene via Stille-type coupling with bis-(tributylstannyl)acetylene.
Referemce:
Bromide – Wikipedia,
bromide – Wiktionary