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James R Smith,Beatrice S L Collins,Matthew J Hesse et al. James R Smith et al.
Using a novel sp2-sp3 hybridized diboron reagent and water as a proton source, a broad range of alkenes undergo hydroboration to provide secondary boronic esters with high regio- and enantiocontrol.
Marcin Odachowski,Amadeu Bonet,Stephanie Essafi et al. Marcin Odachowski et al.
The stereospecific cross-coupling of secondary boronic esters with sp(2) electrophiles (Suzuki-Miyaura reaction) is a long-standing problem in synthesis, but progress has been achieved in specific cases using palladium catalysis.
Christopher Sandford,Ramesh Rasappan,Varinder K Aggarwal Christopher Sandford
The enantiospecific conversion of chiral secondary boronic esters into alkylfluorides is reported. Boronate complexes derived from boronic esters and PhLi were used as nucleophiles, with Selectfluor II as the electrophilic fluorinating agent, to afford alkylfluorides in short reaction times.
Kathryn Feeney,Guillaume Berionni,Herbert Mayr et al. Kathryn Feeney et al.
Boron-ate complexes derived from primary and secondary boronic esters and aryllithiums have been isolated, and the kinetics of their reactions with carbenium ions studied.
Robin Larouche-Gauthier,Tim G Elford,Varinder K Aggarwal Robin Larouche-Gauthier
The addition of an aryllithium reagent to a secondary boronic ester leads to an intermediate boron-ate complex that behaves as a chiral nucleophile, reacting with a broad range of electrophiles with inversion of stereochemistry. Depending o...
Daisuke Imao,Ben W Glasspoole,Véronique S Laberge et al. Daisuke Imao et al.
We report the first example of a coupling reaction of chiral secondary boronic esters generated by the hydroboration of vinyl arenes.
Wesley J Moran,James P Morken Wesley J Moran
[reaction: see text] Rh-catalyzed hydrogenation of prochiral vinyl boronates occurs in an enantioselective fashion in the presence of the chiral ligand Walphos 1. This transformation provides access to chiral secondary organoboronates that ...
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