Reactions of Dry Arenediazonium o‐Benzenedisulfonimides with Triorganoindium Compounds

Abstract

The reaction between various arenediazonium o-benzenedisulfonimides and triorganoindium compounds is described. Depending on the reaction conditions, it is possible to obtain biaryls (16 examples, average yield of 79 %) or diaryldiazenes (18 examples, average yield of 81 %). o-Benzenedi-

Azobenzenes—synthesis and carbohydrate applications

“…The synthesis of symmetrical azobenzene derivatives was effected by: (i) oxidation reactions of aromatic primary amines; [19][20][21][22][23][24][25][26][27][28][29][30] (ii) reduction reactions of aromatic compound having nitro groups; [32][33][34][35][36] (iii) diazo-coupling via diazonium salts; [54][55][56][57][58][59][60][61][62][63][64][65][66][67][68][69][70][71] and (iv) coupling reactions with arenediazonium salts. 100,101 The synthesis of dissymmetrical azobenzene derivatives was effected by: (i) oxidation reactions of aromatic primary amines; 31 (ii) coupling of primary arylamines with nitroso compounds (Mills reaction); [37][38][39][40][41][42][43][44][45][46]…”

“…101 Quinone chemistry is well documented, but only a few studies have been described for the synthesis of azobenzene starting from benzoquinone. 102 Starting from the commercial bis-dimethyl acetal of p-benzoquinone (122), the direct reaction of arylhydrazine 123 afforded the azobenzene 124 in 99% yield (Scheme 47).…”

Enantioselective Nickel‐Catalyzed Cross‐Coupling Reactions of Trialkynylindium Reagents with Racemic Secondary Benzyl Bromides

“…[1,2] The main features of indium reagents are their high versatility, their non-toxicity, and their ability to transfer all three metal-attached groups to the electrophile. A representative example of this usefulness is the particularly effective sp-sp 3 palladium-catalyzed cross-coupling reaction between alkynylindium reagents and benzyl halides (Scheme 1).…”

Reactions of Arenediazonium o‐Benzenedisulfonimides with Aliphatic Triorganoindium Compounds

“…[1] As a follow-up of previous research, in this paper we report a study of the reactions of arenediazonium o-benzenedisulfonimides 1 with aliphatic triorganoindium compounds [triethyl- (2) and tributylindium (3)]. To our great surprise, an aqueous treatment of the reaction mixtures gave, in good yields, N-ethyl-4 and N-butylanilines 5, respectively, and not the expected diazenes.…”

“…Petroleum ether (PE) refers to the fraction boiling in the range 40-70°C. 1 H NMR spectra were recorded with a Bruker Avance 200 spectrometer. Mass spectra were recorded with an HP 5989B mass-selective detector connected to an HP 5890 GC, crosslinked methylsilicone capillary column.…”