Amines synthesis from organoboranes

Sulfonylhydroxylamines and hydroxylamine O-sulfonic acid have found wide apph-cation in synthesis of amines from achiral or chiral organoboranes and boronate esters and the hydroboration-amination methodology is successfully used for direct amination of alkenes. 0-Sulfonyloximes were also found to be good reagents for synthesis of amines from organomagnesium, -copper and -zinc reagents. 

The reaction of trialkylboranes with iV-chloroalkylamines can be used to synthesize a wide variety of functionally substituted dialkylamines in good yields [66,67], and it complements the synthesis of secondary amines via the reaction of trialkylboranes with organic azides. The reaction is analogous to the reaction of chloramine with organoboranes, and presumably occurs via an anionotropic migration of an alkyl group from boron to nitrogen (Scheme 24). 

Synthesis of pure enantiomers. Brown and Singaram1 have reviewed the chiral organoboranes obtained from (+)- and (- )-pinene and their use for synthesis of optically pure amines, halides, hydrocarbons, lithium alkylborohydrides, ketones, aldehydes, a-chiral acids, esters, nitriles, alkynes, and alkenes. 

A convenient synthesis of tert-alkyl amines involves the amination of the methine group with trichloroamine-aluminum chloride. Organoboranes from both hindered and unhindered... 

A little used synthesis of primary alkylamines is the amination of organoboranes. Organoboranes have now been shown to react with chloramine-T prepared in situ from ammonium hydroxide and sodium hypochlorite to give the corresponding amines (Scheme 5). This procedure then represents a mild, one-pot synthesis of various primary alkylamines from alkenes. 

HRu(CO)(PCy3)2Cl for the preparation of organoboranes from vinylsubstituted boronates and olefins, for the stereoselective synthesis of carbazoles, for the intermolecular coupling of cyclic amines and alkenes. ... 

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