A Remarkably Efficient Coupling of Acid Chlorides with Alkynes in Water

Abstract

[reaction: see text] A highly effective direct coupling of acid chloride with terminal alkynes catalyzed by PdCl(2)(PPh(3))(2)/CuI together with a catalytic amount of sodium lauryl sulfate as the surfactant and K(2)CO(3) as the base provided ynones in high yields in water.

Catalyzed Reactions of Alkynes in Water

“…(71)]. [142] In addition, other types of [3 + 2] 1,3-dipolar cycloadditions in water have been reported recently.…”

“…(21)]. [71] No desired product was detected when either Cu(I) alone or Pd(II) alone was used as the catalyst. The use of surfactant was also necessary for the success of this transformation, possibly by temporarily stabilizing the acid chloride.…”

Interface Water Catalysis of the Epoxide Opening

“…[3] Since it was reported that the Diels-Alder reaction can be accelerated by using water as a solvent, instead of organic solvents, [4] considerable attention has been directed toward the development of organic reactions in water-even among water-sensitive compounds. [5] Sharpless et al reported a remarkable phenomenon: they found that the reaction was substantially accelerated when insoluble reactants were stirred in an aqueous suspension; this was denoted as the "on water" condition. [6] For the nucleophilic opening of epoxide in an aqueous suspension, the researchers observed that the reaction was completed overnight after heating at 50 8C, while the reaction in ethanol or under neat conditions required approximately three days to reach completion.…”

Selective chemical reactions in supercritical carbon dioxide, water, and ionic liquids

“…Chen and Li (150) reported an efficient coupling of acid chloride (43) with terminal alkynes (44) using PdCl 2 (PPh 3 )/CuI as co-catalysts and a catalytic amount of surfactant/phase-transfer reagent under basic conditions in water (Scheme 16). Various aryl acid chlorides were coupled with alkyl and arylalkynes with high yields (51Á99%).…”