C-C bond-forming reactions of 2-isocyanobiphenyl·BX3 adducts: spontaneous construction of polycyclic heteroaromatics
Journal
Dalton Transactions
ISSN
1477-9226
1477-9234
Date Issued
2025
Author(s)
Abstract
The syntheses and reactivities of 2-isocyanobiphenyl·BX3 adducts (X = I, Br, Cl) are reported. These adducts undergo unexpected C-H bond-functionalizing cyclization upon heating, yielding phenanthridinium-6-trihaloborate zwitterions. Where X = Cl, an unexpected helical polycyclic boronium salt is formed via a competing pathway. Mechanistic details are probed experimentally and computationally.
Publisher
Royal Society of Chemistry (RSC)
Type
journal article