Copper(i) iodide–DMAP catalyzed homo- and heterocoupling of terminal alkynes

Abstract

A practical and efficient catalytic system comprising CuI and DMAP has been developed for the oxidative homo-and heterocoupling of terminal alkynes under aerobic conditions at room temperature. The catalytic utility of DMAP for efficient oxidative coupling of terminal alkynes has been explored. The CuI-DMAP catalytic system avoids the need for excess base and specialized ligands in oxidative coupling. Short reaction times make this approach economical and environmentally friendly.

Unique distal size selectivity with a digold catalyst during alkyne homocoupling

“…The heterocoupling of terminal alkynes has been reported in the literature with different copper catalysts but, in all cases, a five-times amount of one of the alkynes must be added to achieve good yields of heterocoupling product [47][48][49][50] . Otherwise, with a one-to-one molar ratio of alkynes, a statistical 1:2:1 molar ratio of homo:hetero:homocoupled products, or a 1:1:1 molar ratio in some cases, is obtained [47][48][49][50] . In addition, the two alkynes must be differentiated either electronically (aryl or heteropropargyl versus alkyl alkynes, activated versus deactivated aryl alkynes) or sterically near the triple bond (linear versus bulky alkynes).…”

Unprecedented one-pot multicomponent synthesis of propargylamines using Amberlyst A-21 supported CuI under solvent-free conditions

“…A compromise of 10 mol%, however, seemed to be sufficient. 66,67 For this reason, it was decided that an excess of 0.5 mmol alkyne would be the best approach to ensure that an optimum yield is maintained (entry 7, Table 2). In this regard, it was decided that 10 mol% catalyst and a temperature of 100 °C (entry 2, Table 2) should be adopted for the trials that followed.…”

Accelerating Effect of DMAP on CuI Catalyzed Buchwald‐Hartwig C‐N Coupling: Mechanistic Insight to the Reaction Pathway

“…In the recent past, DMAP has been proven to be an excellent ligand for metal catalyzed organic transformations . It has several advantages over the other ligand due to its commercial availability, low cost and greater stability.…”

“…In the recent past, DMAP has been proven to be an excellent ligand for metal catalyzed organic transformations. [27][28][29][30][31] It has several advantages over the other ligand due to its commercial availability, low cost and greater stability. Moreover, DMAP has very high neucleophilic character [32] for which it acts both as catalyst as well as excellent ligand.…”