Formation of 1,3-diynes, 1,3-dienes, and biphenyls via the copper(II) nitrate mediated coupling of organotin compounds

Synthesis of ‘thianthrene dimer’ by the coupling reaction of stannylthianthrenes in the presence of copper catalysts

“…Recently, Ogawa et al 9b reported the synthesis of 1,9 0 -disubstituted thianthrene by Negishi coupling reaction. Meanwhile, on the coupling reaction of aryl groups, 10,11 alkynyl, 10 alkenyl, 10,12 and vinyl 13 groups via stannanes in the presence of Cu(NO 3 ) 2 $3H 2 O. It is well known that the protocols were highly effective and versatile, another using copper catalysts, such as Cu(NO 3 ) 2 $3H 2 O and CuCl, were used in THF or DMF condition.…”

Trisannelated Benzenes by Cyclotrimerization of Bromostannylalkenes

“…[12] 6a-c The mechanism of cyclotrimer formation under the catalytic influence of copper(1r) nitrate is still unclear. Based on similar experiments and literature reports [13] it is possible to conjecture tincopper transmetalation with formation of an organocopper species that evolves into a vinyl radical.…”

One-Pot, Stereoselective Synthesis of Trisubstituted 1,3-Dienes by Hydromagnesiation–Cross-Coupling Tandem Reaction of Alkylarylacetylenes with Alkenyl Iodides

“…[1] The synthesis of 1,3-dienes for use in the Diels-Alder reaction is still an important challenge in organic synthesis, [2] although other elegant uses of these compounds have been developed. [3] Conjugated dienes are usually prepared by utilizing either a Wittig-type approach [4] or through transition-metal-catalyzed coupling reactions of stereodefined vinyl halides with vinyl organometallic compounds. [5] Whitby et al reported the insertion of 1-lithio-1-halo-butadiene into organozirconocenes derived from the hydrozirconation of alkynes, providing a stereocontrolled synthesis of (1E,3Z)-1,3-dienes.…”