Fluorinated organoboron

Of particular sigiuficance in the chemistry of organoboranes is their behavior as Lewis acids, which is a result of the empty / -orbital of tricoordinate boron. Much recent effort has been devoted to the synthesis and development of highly Lewis-acidic organoboron compounds through introduction of fluorinated organic substituents. Boron can reach the... 

Most chiral organoboron Lewis acids reported to date are based on an organoborane that is attached to a chiral organic moiety such as a diol, aminoalcohol, or other readily available chiral substrates.Organoboron derivatives recently used as catalysts in enantioselective Diels-Alder reactions include the family of chiral acyloxyboranes (CAB) with (196) and (197) as representative examples and various cyclic boronic esters such as (198) and (199). An interesting system that combines the favorable Lewis acid properties of fluorinated arylboranes with a chiral Bronsted acid has been developed by Ishihara and Yamamoto. The Bronsted acid-assisted chiral Lewis acids (BLA) (200) was found to be highly effective in enantioselective cycloadditions of Q ,jS-enals with various dienes. The presence of the Bronsted acid functionality leads to significant acceleration of the reaction. 

A range of organoboron compounds can be readily fluorinated using copper and palladium catalysts [84, 93-95]... 

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