Copper(II) Acetylacetonate: An Efficient Catalyst for Huisgen‐Click Reaction for Synthesis of 1,2,3‐Triazoles in Water

Abstract

An efficient and green copper(II) acetylacetonate-catalyzed protocol for the Huisgen-click reaction in water at 100 ℃ has been established. The protocol was not only suitable for the reaction between organic azides and alkynes, but also suitable for one-pot three-component reaction among alkyl halides, NaN 3 and alkynes.

Pd/C-Catalyzed Carbonylative Synthesis of 2-Aminobenzoxazinones from 2-Iodoaryl Azides and Amines

“…On the other hand, transition-metal-catalyzed carbonylation reactions using low cost and accessible carbon monoxide as the C1 building block have been widely applied in organic synthesis, and such types of reaction have been used for constructing various biologically active heterocycles as well . Moreover, azides are interesting compounds and have been broadly utilized in the synthesis of functionalized 1,2,3-triazoles through click reaction . Compared with traditional methods for generating 2-amino-substituted benzoxazinones, using azides as the substrates to construct N-containing heterocycles could avoid the use of external oxidants and only forms N 2 as the byproduct. , Combining the recent work of our group with the continued exploration of palladium-catalyzed carbonylation reactions, herein we describe the application of 2-iodoaryl azides and amines as substrates in palladium-catalyzed carbonylative transformation.…”

Single-Molecule Orthogonal Double-Click Chemistry—Inorganic to Organic Nanostructure Transition

“…Uncatalyzed azide–yne reactions show measurable conversions in approximately 4 h at room temperature but typically proceed to maximum yield in ∼24 h at room temperature . Catalyzed reactions at elevated temperatures require minutes to hours to obtain the maximum yield . Nguyen et al have reported “ultrafast” reaction times for thiol–ene reactions, noting a cure after 2 min of exposure times, while a prior report for photoactivated thiol–ene of poly­(mercapto-functional)­siloxane cross-linking of vinylsiloxane resins indicated time scales of ∼2 min .…”

Recent Progress of Cu-Catalyzed Azide-Alkyne Cycloaddition Reactions (CuAAC) in Sustainable Solvents: Glycerol, Deep Eutectic Solvents, and Aqueous Media

“…In spite of the well documented viability of CuAAC reactions in pure water under ligandand additive-free conditions [63], the finding of highly efficient CuAAC procedures catalyzed by commercially available Cu salts is an active research area. In this sense, impressive substrate scope was reached recently by Jiang and Xu using Cu(II) catalysts in very low metallic charges (see Scheme 7a,b) [64,65]. Both Cu(II) catalysts (CuSO 4 •5H 2 O [64] or Cu(acac) 2 [65]) required harsh conditions.…”

“…In this sense, impressive substrate scope was reached recently by Jiang and Xu using Cu(II) catalysts in very low metallic charges (see Scheme 7a,b) [64,65]. Both Cu(II) catalysts (CuSO 4 •5H 2 O [64] or Cu(acac) 2 [65]) required harsh conditions. In contrast, they proved efficient for the three-component synthesis of 1,4-disubstituted 1,2,3-triazoles starting from terminal alkynes, NaN 3 and organic halides (R-X).…”