The cross-coupling reaction of vinylindiums generated via hydroindation of terminal alkynes with diaryliodoniums salts

Diaryliodonium Salts: A Journey from Obscurity to Fame

“…A reductive arylation of terminal alkynes using indium trichloride and sodium borohydride was reported by Xue and co-workers in 2006 (Scheme 29). [127] The reaction was successful for a wide range of aromatic alkynes, furnishing the (E)-alkene as the major product with minor amounts of the (Z)-and 1,1-substituted alkenes as byproducts.…”

Chemistry of Polyvalent Iodine

“…In more recent papers, the electrophilic arylations of sodium arenesulfinates,725 potassium carbonotrithioates,726 and benzazoles727 using diaryliodonium salts in ionic liquids, and the arylations of anilines,728 sodium tetraphenylborate729 and vinylindiums730 have been reported.…”

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

“…Inspired by previous results, desyl chloride 3 (2-chloro-1,2-diphenylethanone), which had successfully promoted the Csp À Csp 3 oxidative cross-coupling, [21] was chosen as the oxidant. Desyl chloride 3 was expected to add oxidatively to Pd(0) to form C-bonded Pd-enolate 3-I, which could tautomerize possibly to O-bonded Pd-enolate 3-II (Scheme 2).…”

“…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).…”

“…The strategy has been successfully applied in cross-coupling of Csp À Sn reagents and Csp 3 À Zn reagents. [21] Herein, we report our extension to make Csp 2 À Csp 3 bonds by this strategy, in which arylzinc reagents and alkylindium reagents were successfully cross-coupled with high selectivities under mild conditions.…”