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Triphenyl bismuth bisperfluorooctanesulfonate is an air- and water-stable Lewis acid. It exhibits high catalytic efficiency for the synthesis of nitrogen heterocycles such as diindolylmethane derivatives, dihydropyrimidinones, dihydropyridines and 1,2-disubstitued benzimidazoles under mild condition. Furthermore, it can be reused without loss of activity in a test of five cycles.This catalytic system affords a simple and efficient way for the synthesis of N-containing compounds. [ABSTRACT FROM AUTHOR]

In the synthesis of binuclear organobismuth complexes ( 1- 6) through treatment of organobismuth chlorides with NaOH or Na2S⋅9H2O, the two 5,6,7,12-tetrahydrodibenz [ c,f][1,5]azabismocine frameworks are cross-linked by either a sulfur or an oxygen atom. The complexes ( 1- 6) show high catalytic efficiency in the synthesis of cyclic carbonates from 2-(chloromethyl)oxirane and CO2. Compared with their precursor chlorides ( 7- 9), methoxide 10 and methanethioate 11 which are mononuclear organobismuth complexes, the binuclear organobismuth complexes show higher cooperative catalytic effect. However, the complexes with an oxygen bridge ( 1- 3) are not stable in air and lose their catalytic efficiency because of hydrolysis or CO2 adsorption (forming organobismuth carbonates in the latter case). Nonetheless, the binuclear organobismuth complexes ( 4- 6) with a sulfur bridge are highly stable in air and can be applied in the synthesis of cyclic carbonates (with the co-presence of Bu4NI) across various kinds of epoxides, thus exhibiting satisfactory efficiency and selectivity. [ABSTRACT FROM AUTHOR]

In the direct Mannich reaction and synthesis of α,β-unsaturated ketones, the use of organobismuth complexes as catalysts leads to high diastereoselectivity and products of single transconformation. In this paper, we illustrate the relationship between structure and catalytic activity as well as diastereoselectivity of organobismuth complexes having a 5,6,7,12-tetrahydrodibenz [c,f][1,5]thiobismocine framework as well as bearing a butterfly-shaped sulfur-bridged ligand and tunable anions. With the exposed bismuth center acting as a Lewis acid site and the uncoordinated lone pair electrons of sulfur as a Lewis base site, the cationic organobismuth complexes work as bifunctional Lewis acid/base catalysts. Due to the steric influence of the butterfly-shaped structure and synergistic effect of Lewis acid and Lewis base centers, the complexes can direct substrate attack in organic synthesis. By adjusting the electron-withdrawing ability of the counter anions, the S–Bi bond strength can be regulated, leading to a significant change in Lewis acidity and Lewis basicity as well as catalytic activity. Through synergistic modulation of the above effects, one can control the diastereoselectivity of the organobismuth complexes for the generation of a single diastereoisomer. [ABSTRACT FROM AUTHOR]

The catalyst system that comprises an air-stable bifunctional Lewis acidic/basic organobismuth complex and [Bmim]BF4is highly efficient in the cross-condensation of aldehydes with ketones. Through switching the reaction from homogeneous to heterogeneous, the system shows facile separation ability and facile reusability. [ABSTRACT FROM AUTHOR]

An air-stable cationic organobismuth complex was successfully synthesized and found to show high catalytic efficiency in the direct diastereoselective Mannich reaction in water. [ABSTRACT FROM AUTHOR]

Review: 76 refs. [ABSTRACT FROM AUTHOR]

The article presents chemical equation for the article "Air-Stable Organobismuth(V) Bisperfluorooctanesulfonate as an Efficient Catalyst for the Synthesis of N-Containing Compounds" by P. Wang and others, published in the journal "Advanced Synthesis & Catalysis" in 2016.