Selective Linear Triene Formation from Different Alkynes using Zr/Cu system

Abstract

Selective synthesis of linear trienes from three different alkynes was achieved in one-pot procedure using the Zr/Cu system. Zirconacyclopentadiene prepared from two different alkynes such as an alkyl-substituted alkyne and an aryl-substituted alkyne reacted with NCS gave chlorodienylzirconocene. It reacted with the third alkyne with electron-withdrawing groups in the presence of CuCl to afford the corresponding linear triene.

Ru(0)-Catalyzed Direct Coupling of Internal Alkynes with Conjugated Dienes: An Efficient Access to Conjugated Trienes

“…Conjugated trienes are important motifs in many natural products, biologically active compounds, and electronic materials . They are conventionally prepared by stoichiometric reactions such as Wittig and Horner–Wadsworth–Emmons reactions and alkyne/zirconacyclopentadiene coupling Scheme gives an overview of the current transition-metal-catalyzed approaches.…”

Niobium- and zirconium-catalyzed reactions of substituted 2 alkynylamines with Et2Zn

“…Metal alkyne complexes of Ti, [1][2][3][4][5][6][7][8][9][10] Zr, [11][12][13][14][15] Ta, [16][17][18][19][20][21][22] and Nb [23][24][25][26][27][28][29][30] have a high value for organic synthesis, as they are efficient precursors for the preparation of a broad range of organic compounds. A considerable contribution to the chemistry of zirconocenealkyne derivatives was made by Buchwald [31][32][33] and Negishi.…”

NbCl5-Mg Reagent System in Regio- and Stereoselective Synthesis of (2Z)-Alkenylamines and (3Z)-Alkenylols from Substituted 2-Alkynylamines and 3-Alkynylols

“…Rosenthal and Burlakov [ 1 , 2 ] have performed studies on the synthesis of titanocene and zirconocene alkyne complexes based on the pioneering works done by Vol’pin and Shur [ 3 , 4 ]. The synthesized transition metal alkyne complexes are of value because these metallacyclopropenes are a source of reactive metallocenes serving as precursors for the synthesis of various organic compounds [ 1 , 4 , 5 , 6 , 7 , 8 , 9 , 10 , 11 , 12 , 13 , 14 , 15 , 16 , 17 , 18 ]. As regards the synthesis of niobium alkyne complexes, the chemistry of low-valent niobium complexes with unsaturated substrates is poorly known.…”