Hypervalent Bromine for Novel Synthesis

A highly efficient and sustainable route to cyclic and chiral *3-bromane synthesis and their synthetic utilization has been proposed by the application of electric current. The use of electrons as reagent in such transformations would replace the use of stoichiometric toxic reagents and unwanted by-product formation and thereby increase the yield and the potency of the process. Owing to the enhanced reactivity of bromanes over iodanes would make the resulting *3-bromanes a versatile reagent for the fluoroalkylation reactions under milder reaction conditions. The synthesized fluoroalkyl-*3-bromane will be characterised by the various spectroscopic techniques. First time, the stereoselective fluoroalkylation strategies will be disclosed by using asymmetric *3-bromane salts. The reactivity of the chiral bromane salts will also be evaluated by accessing divergent chiral environment. The application of cyclic *3-bromanes will be demonstrated by the late stage fluoroalkylation at the primary and secondary benzylic sites. The successful outcome of the benzylic fluoroalkylation strategy will be further extended to the benzylic fluoroalkylation of commercially available drug molecules under flow conditions. Finally, the challenging aspect of microreactor technology would be incorporated for an automated self-optimization in late stage modification of peptides as well as reaction of captopril, a widely used antihypertension
drug, via isotopic fluoroalkylation and alkynylation with the aid of HPLC and quantitative LC-MS. Detailed mechanistic studies for the generation of cyclic and chiral *3-bromane as well as their synthetic utilization in pharmaceutically useful molecule synthesis will be performed with spectroscopic evidences.