Dimeric boroles: effective sources of monomeric boroles for heterocycle synthesis

Abstract

Dimeric boroles as thermal sources of monomers.

One tool to bring them all: Au-catalyzed synthesis of B,O- and B,N-doped PAHs from boronic and borinic acids

“…This way, boroles or 9borafluorenes have been converted to 2,1-B,N/2,1-B,Obenzenes or 10,9-B,N/10,9-B,O-phenanthrenes, respectively. 41,53,54,[80][81][82][83][84][85] Inspired by the well-established oxypalladation of alkynes and Sheppard's above-mentioned work, 43 our group herein discloses a straightforward protocol for the synthesis of (B,N)nand (B,O)n-PAHs. The main structural motif present in all synthetic intermediates employed is that of an o-alkynylsubstituted aryl boronic or borinic acid (Scheme 3).…”

Boron and Silicon-Substituted 1,3-Dienes and Dienophiles and Their Use in Diels-Alder Reactions

“…Martin and co-workers have continued their work on the reactions of the 1-phenyl-2,3,4,5-tetramethylborole dimer ( 57 ) this year ( Scheme 18 ) [ 19 ]. Unlike pentaphenylborole, the tetramethylboroles dimerize as outlined above, and this dimer ( 57 ) was heated with a number of potential cycloaddition/cyclization partners in this study.…”

2,5-Bis-trimethylsilyl substituted boroles

“…These dimers can provide a source of monomeric borole synthons upon thermal treatment. [49][50][51] With free boroles being so reactive, to date, their synthesis and successful isolation is limited to relatively few substituents around the central C 4 B cycle. 52 Most reports on free borole chemistry discuss pentaaryl boroles 34,53,54 and particularly (PhC) 4 BAr for which reliable synthetic protocols exist.…”