Willcox, Dominic R.; Nichol, Gary S.; Thomas, Stephen P. published the article 《Borane-Catalyzed C(sp3)-F Bond Arylation and Esterification Enabled by Transborylation》. Keywords: borane boronate catalyst dehydrocoupling aryl fluoride fluoroalkane aromatic hydrocarbon; diarylmethane preparation dehydrocoupling aryl fluoride aromatic hydrocarbon borane catalyst.They researched the compound: 1-(Bromomethyl)-4-iodobenzene( cas:16004-15-2 ).Application In Synthesis of 1-(Bromomethyl)-4-iodobenzene. Aromatic heterocyclic compounds can be divided into two categories: single heterocyclic and fused heterocyclic. In addition, there is a lot of other information about this compound (cas:16004-15-2) here.
The activation and functionalization of carbon-fluorine bonds represent a significant synthetic challenge, given the high thermodn. barrier to C-F bond cleavage. Stoichiometric hydridoborane-mediated C-F functionalization has recently emerged, but is yet to be rendered catalytic. Herein, the borane-catalyzed coupling of alkyl fluorides with arenes (carbon-carbon bond formation) and carboxylic acids (carbon-oxygen bond formation) has been developed using transborylation reactions to achieve catalytic turnover. Successful C-C and C-O coupling across a variety of structurally and electronically differentiated arenes and carboxylic acids was achieved using 9-borabicyclo[3.3.1]nonane (H-B-9-BBN) as the catalyst and pinacolborane (HBpin), with broad functional group tolerance. Exptl. and computational studies suggest a mechanistic dichotomy for the carbon-carbon and carbon-oxygen coupling reactions. B-F transborylation (B-F/B-H metathesis) between F-B-9-BBN and HBpin enabled catalytic turnover for carbon-carbon bond formation, whereas direct exchange between the alkyl fluoride and acyloxyboronic ester (C-F/B-O metathesis) was proposed for carbon-oxygen coupling, where H-B-9-BBN catalyzed the dehydrocoupling of the carboxylic acid with HBpin.
Although many compounds look similar to this compound(16004-15-2)Application In Synthesis of 1-(Bromomethyl)-4-iodobenzene, numerous studies have shown that this compound(SMILES:IC1=CC=C(CBr)C=C1), has unique advantages. If you want to know more about similar compounds, you can read my other articles.
Reference:
Piperazine – Wikipedia,
Piperazines – an overview | ScienceDirect Topics