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Boronic acid solution speciation can be controlled during the Suzuki-Miyaura cross-coupling of haloaryl N-methyliminodiacetic acid (MIDA) boronic esters to enable the formal homologation of boronic acid derivatives. The reaction is contingent upon control of the basic biphase and is thermodynamically driven: temperature control provides highly chemoselective access to either BMIDA adducts at room temperature or boronic acid pinacol ester (BPin) products at elevated temperature. Control experiments and solubility analyses have provided some insight into the mechanistic operation of the formal homologation process.

The iodides (II) and (X), which are available in good yields, efficiently undergo Suzuki—Miyaura coupling with a number of aromatic trifluoroborates and some arylboronic acids.

The development of a dehydrofluorination/zincation and Negishi coupling protocol is presented.

The condensation—oxidation of dialdehydes (I) and (V) with diamines gives the corresponding 1,3- and 1,4-diamidines.

Enantiopure bromonium ions may be generated from enantiopure bromohydrins and derivatives, they can be trapped with an in situnucleophile to give enantiomerically pure products.

(±)-iso-Amarine is a potent organocatalyst at 1 mol % loading for both the bromoacetoxylation of alkenes with added acetic acid and bromolactonisation of unsaturated carboxylic acids with stoichiometric NBS as the electrophilic bromine source. A simple bromoamidine with an N–Br bond has been characterised crystallographically for the first time. Asymmetric induction in the bromination reactions with enantiopure amidines was zero.