Tris(polymethoxyphenyl)bismuth derivatives: Synthesis and reactivity

Synthesis, Properties Characterization and Applications of Various Organobismuth Compounds

“…Finet et al investigated the synthesis of tris(polymethoxyphenyl)bismuth derivatives and their utilization in C -, N - and O -arylation reactions [ 9 ]. These bismuth compounds were prepared with electron-rich aryl groups (polymethoxyaryl fragments) which could be effectively transferred in arylation reactions, breaking the commonly accepted stereotype that organobismuth arylation agents were effective only for the transfer of aryl groups with electron-poor and electron-neutral substituents.…”

“…For the sake of the goal of environmentally benign reactions, the use of non-toxic reagents has been identified as one of the best procedures in organic synthesis. Thus, a large number of organobismuth mediated reactions had been studied and the fascinating role of organobismuth reagents had been revealed [ 9 , 36 , 38 , 47 ]. Many organic reactions such as C -, N - and O -arylation reactions, cross-coupling reactions, polymer reactions, asymmetric synthetic reactions and other special reactions with organobismuth reagents, especially many novel reactions were summarized in the following sections.…”

“…Arylation reactions with organobismuth reagents were developed relatively early. Organobismuth reagents allow three major types of arylation reactions: (a) C - and O -arylation via a covalent intermediate; (b) O -arylation under neutral conditions; (c) O - and N -arylation under copper catalysis [ 9 , 38 ]. Previous reviews about various arylation reactions with organobismuth reagents were focused on both the bismuth(V) and bismuth(III) compounds.…”

“…A number of reports [ 4 , 5 , 6 , 7 , 8 ] on these compounds have mentioned their positive role in a variety of synthetic transformations or polymerizations, acting as reagents or catalysts. Bismuth is relatively low-cost, easily available, and it presents the lowest toxicity among the heavy non-radioactive main group elements [ 9 , 10 ]. These attractive features, combined with the Green Chemistry principles, have made many inorganic and organic derivatives of bismuth broadly and safely used in organic synthesis, catalysis, materials and even medicine [ 11 , 12 , 13 , 14 , 15 , 16 ].…”

“…Hence, organobismuth compounds have emerged as an important class of organometallic compounds that have seen increased applications in different areas over the last 20 years [ 8 , 17 ], as organobismuth chemistry has developed rapidly and some novel organobismuth compounds have been reported [ 18 , 19 , 20 , 21 ]. Many types of organobismuth compounds have been proven to be efficient reagents in C -, N - and O -arylation reactions [ 9 ], benzoylation reactions [ 22 ], cross-coupling reactions [ 10 ], etc. However, the organometallic chemistry of bismuth has developed relatively slowly compared to that of other main group metals due to the instability of the bismuth carbon bond [ 23 , 24 ].…”