Dutta, Shubham; Yang, Shengwen; Vanjari, Rajeshwer; Mallick, Rajendra K.; Gandon, Vincent; Sahoo, Akhila K. published an article in Angewandte Chemie, International Edition. The title of the article was 《Keteniminium-Driven Umpolung Difunctionalization of Ynamides》.Computed Properties of C6H5BBr2O2 The author mentioned the following in the article:
A three-component Pd-catalyzed coupling of ynamides, aryl diazonium salts, and aryl boronic acids for the synthesis of novel triaryl-substituted enamides is described. This transformation represents the first example of an umpolung regioselective unsym. syn-1,2-diarylation/aryl-olefination of ynamides. The aryl moieties of the diazonium salt (electrophile) and boronic acid (nucleophile) are explicitly incorporated in the electrophilic α- and nucleophilic β-position, resp., of the ynamide, resulting in a single isomer of the N-bearing tetrasubstituted olefin. The scope is broad (68 examples), showing excellent functional-group tolerance. DFT calculations substantiate the rationale of the mechanistic cycle and the regioselectivity. The chemoselectivity and synthetic potential of the enamide products were also studied.3,4-Dibromophenylboronic acid(cas: 1228180-83-3Computed Properties of C6H5BBr2O2) was used in this study.
3,4-Dibromophenylboronic acid(cas: 1228180-83-3) belongs to organobromine compounds.Depending on the type of carbon to which the bromine is bonded, organic bromide could be alkyl, alkenyl, alkynyl, or aryl. Computed Properties of C6H5BBr2O2 Dehydrobromination, Grignard reactions, reductive coupling, Wittig reaction, and several nucleophilic substitution reactions are some of the principal reactions which involve organic bromides.
Referemce:
Bromide – Wikipedia,
bromide – Wiktionary