Document Type

Poster Presentation

Publication Date

2025

Abstract

Catechol borane, pinacol borane, and 9-borabicyclo[3.3.1]nonane, 9-BBN, are versatile cyclic borane (CB) hydroboration agents.1,2 The borinates/boronates obtained from their reactions with alkenes and alkynes are good candidates for various Suzuki-Miyaura coupling reactions–a very important reaction that has been used in the synthesis of multiple drugs. However, CBs do have a few drawbacks, such as the high cost of 9-BBN, and are relatively unreactive compared to their dialkylborane analogs. Furthermore, none of these boranes provides the chiral environment required for asymmetric induction by themselves.3,4 A quick survey of natural products revealed many terpene dienes such as limonene, ɑ-phellandrene, and valencene that could be used in place of cyclooctadiene with the potential of producing cheaper and possibly chiral reagents. Expanding on previous findings that exhibit 2-BBN’s reducing capabilities after hydroboration with BDMS and limonene, the purpose of this project is to (1) examine CBs from other terpenes, primarily (-)-ɑ-phellandrene, with diene functionalities for utility as 9-BBN alternatives and (2) effectively scale-up and isolate the hydroborated diene 9-BBN analog for simplification of future reduction reactions, where (3) in the case of a successful reduction with a CB, asymmetric induction may be examined and optimized.

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