Divergent synthesis of stereodefined benzocyclobutene and indoline derivatives via sequential Cu- and Pd-catalysis

Abstract

The synthesis of stereodefined benzocyclobutene (BCB) and indoline derivatives is described. Both scaffolds can be accessed using the same palladium catalyst from a common homoallylic borylated amine intermediate. Notably, to our knowledge this represents the first Suzuki-mediated four-membered ring closure. The common intermediate is easily accessed using the Cu-catalysed borylative technology developed in our laboratory. Preliminary results on an enantioselective variant are described. The products can easily be further manipulated into advanced material industrial intermediates. Overall, this sequential approach offers an unprecedented, mild, and general access to BCBs for which very few synthetic options are currently available, and a rapid access to medicinally relevant indolines.

Date of Award	1 Aug 2021
Original language	English
Awarding Institution	The University of Manchester
Supervisor	David Procter (Supervisor) & Gregory Perry (Supervisor)