Sustainable and practical formation of carbon–carbon and carbon–heteroatom bonds employing organo-alkali metal reagents

Abstract

Metal-catalysed cross-coupling reactions are amongst the most widely used methods to directly construst new bonds. In this connection, sustainable and practical protocols, especially transition metal-catalysed cross-coupling reactions, have become the...

The Versatile and Strategic O-Carbamate Directed Metalation Group in the Synthesis of Aromatic Molecules: An Update

“…To conform with trends in industry and academia, − research has gone into the development of organometallic chemistry which uses fewer polluting reagents, less harsh conditions, and promotes the use of more sustainable and circular chemistry. − Thus, far, regarding the D o M and A o F of aryl O -carbamates, this work has mainly focused on conducting the reactions under aerobic conditions using greener solvents. Ghinato et al were the first to report efficient protocols for enabling D o M using and A o F of ArOAms with hindered lithium amide metalating agents, using cyclopentyl methyl ether (CPME) as sustainable reaction solvent under aerobic conditions.…”

A fruitful century for the scalable synthesis and reactions of biphenyl derivatives: applications and biological aspects

“…Negishi reported an easy regio- and chemoselective method for the synthesis of unsymmetrical biaryl using an aryl–aryl coupling process that is catalyzed by nickel salts. 25,97 Treatment of cyanophenyl zinc bromide 79 with o -iodobenzoate 1 in the presence of palladium bis(dibenzylideneacetone) (Pd(dba) 2 ) and tris- o -furylphosphine (tfp) furnished biphenyl derivatives 2 . 98 In 2009, Phapale and Cárdenas 99 discovered that Ni-based catalysts (Ni(acac) 2 /PPh 3 ) facilitate coupling between aryl zinc chlorides 79 and haloarenes 1 affording biphenyl derivatives 2 .…”

Synthesis and Reactivity of Dipalladated Derivatives of Terephthalaldehyde

“…Arylpalladium complexes are crucial intermediates in a wide range of palladium-catalyzed carbon–carbon and carbon-heteroatom bond-forming reactions, which have facilitated the efficient and selective construction of complex organic molecules. − Consequently, the synthesis, characterization, and reactivity of these complexes remain a very active field of research. − Organic substituents ortho to the Pd atom may be involved in this chemistry, yielding novel structures and potentially useful organic compounds. − ,, We have been interested in exploring the extension of this chemistry to di- , and tripalladated − benzene derivatives ortho -substituted at each Pd(II) center. Thus, our group has reported the synthesis and reactivity of mono-, di-, and tripalladated derivatives of mesitylene, , benzenetricarboxaldehyde, and tris(styryl)benzene (Chart A), as well as dipalladated derivatives of 2,5-distyrylbenzene , (Chart B).…”