First Nickel-Catalyzed 1,4-Conjugate Additions to α,β-Unsaturated Systems Using Triorganoindium Compounds

2,6-Di(4-t-butylphenyl)phenyl-group 13 organometallic compounds

“…Correspondingly, other R 2 GaX compounds (R = 2,6-Ph 2 C 6 H 3 ; X = I [16], and R = 2,6-Mes 2 C 6 H 3 ; X = Cl [22], Br [14]), all have distorted trigonal planar environments around the gallium metal center. The C-Ga-Br bond angles in With the growing utility of triorganoindium compounds for fundamental organic transformations such as conjugate addition [23], cross-coupling [24][25][26], and allylic substitution reactions [27,28], and the ubiquitous use of m-terphenyl ligands in organometallic-group 13 chemistry, it is noteworthy that there are no reports of tris(m-terphenyl)indium compounds. Compound 4, the first tris (m-terphenyl)group 13 compound, is noteworthy.…”

Highly Selective Palladium‐Catalyzed Oxidative Csp2Csp3 Cross‐Coupling of Arylzinc and Alkylindium Reagents through Double Transmetallation

“…Unfortunately, all attempts using Ar À Sn reagents and R alkyl À Zn reagents resulted in poor yields and poor selectivities for cross-coupled products. Satisfactorily, organoindium reagents (R 3 In, R = alkyl, alkenyl, alkynyl, aryl), possessing interesting chemical properties including a low first oxidation potential, stability under aqueous conditions and low toxicity, [21,[23][24][25][26][27][28][29][30][31][32][33] turned out to be a good option, and the combination of (4-chlorophenyl)zinc(II) chloride 1b and triphen-A C H T U N G T R E N N U N G ethylindium 2f with PdCl 2 A C H T U N G T R E N N U N G (dppf) as catalyst displayed a promising result. The cross-coupled product was obtained in 78% yield (Table 1, entry 6).…”

Cu‐ and Ni‐Catalyzed Conjugated Additions of Organozincs and Organoaluminums to α,β‐Unsaturated Carbonyl Compounds

“…Interestingly, there are very few reports of their use in conjugated additions; the such first report, which appeared in 1998, involved the conjugated additions of triorganoindiums (n-butyl, t-butyl, and phenyl) to vinylmethylketone, acrylate, and acrylonitrile catalyzed by a nickel complex [51] addition of diarylindium hydroxides to various α,β-unsaturated ketones, esters, and nitriles [52].…”