Stereoselective Suzuki coupling reaction of an α-bromo-α-fluoro-β-lactam
A new strategy has been developed for the synthesis of α-aryl-α-fluoro-β-lactams via the Suzuki cross-coupling of α-bromo-α-fluoro-β-lactam with a range of different aryl-(9-BBN) reagents. This method provides facile access to multisubstituted α-fluoro-β-lactams in a diastereoselective manner. The synthetic utility of α-bromo-α-fluoro-β-lactam has been demonstrated by the arylation of α-bromo-α-fluoro-β-lactam.
“Inverse” Frustrated Lewis Pairs: An Inverse FLP Approach to the Catalytic Metal Free Hydrogenation of Ketones
For the first time have boron-containing weak Lewis acids been demonstrated to be active components of Frustrated Lewis Pair (FLP) catalysts in the hydrogenation of ketones to alcohols. Combining the organosuperbase (pyrr)3P=NtBu with the Lewis acid 9-(4-CF3-C6H4)-BBN generated an “inverse” FLP catalyst capable of hydrogenating a range of aliphatic and aromatic ketones including N-, O- and S-functionalized substrates and bio-mass derived ethyl levulinate. Initial computational and experimental studies indicate the mechanism of catalytic hydrogenation with “inverse” FLPs to be different from conventional FLP catalysts that contain strong Lewis acids such as B(C6F5)3.
Mummadi, Suresh,Brar, Amandeep,Wang, Guoqiang,Kenefake, Dustin,Diaz, Rony,Unruh, Daniel K.,Li, Shuhua,Krempner, Clemens
supporting information
p. 16526 - 16531
(2018/10/20)
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