2021
DOI: 10.1002/aoc.6401
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Tris‐isocyanide copper(I) complex enabling copper azide‐alkyne cycloaddition in neat conditions

Abstract: The three‐coordinated homoleptic Cu(I) complex with 2,6‐dimethylphenyl isocyanide in the coordination sphere was easily synthesized and isolated as tetrafluoroborate salt. The structure of the compound was determined by single‐crystal X‐ray diffraction. The complex is highly stable, active and selective toward the copper‐catalyzed azide‐alkyne cycloaddition, working in neat conditions and in the absence of bases at room temperature. Substrate scope was assessed by testing several different alkynes and azides. … Show more

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Cited by 12 publications
(20 citation statements)
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“…Summing up, given our interest in palladium catalysed carbonylation reactions 14 and sustainability, 15 we realized that the identification of a halogen-free synthetic strategy for the synthesis of alkyl arylacetates from benzyl acetates could represent a valuable alternative to industrial practices adopted to date. With this in mind, the unprecedented carbonylation of benzyl acetates is herein discussed (Scheme 1e).…”
Section: Introductionmentioning
confidence: 99%
“…Summing up, given our interest in palladium catalysed carbonylation reactions 14 and sustainability, 15 we realized that the identification of a halogen-free synthetic strategy for the synthesis of alkyl arylacetates from benzyl acetates could represent a valuable alternative to industrial practices adopted to date. With this in mind, the unprecedented carbonylation of benzyl acetates is herein discussed (Scheme 1e).…”
Section: Introductionmentioning
confidence: 99%
“…The distance from the Cu1 to the centroid of the imidazole plane (Cu–π imidazole ) is only 3.024 Å and the deviation of Cu1 from the plane defined by the coordinating P1, P2 and I1 atoms is 0.2285 Å, larger than that found in other three-coordinate complexes. 27,28,45 Similarly, in complex 2 , the Cu–π imidazole distance is 3.044 Å, which induces a slightly shorter distance (0.2189 Å) between Cu1 and the P1–P2–Br1 plane than that of 1 . Furthermore, the Cu–π imidazole distance is increased to 3.317 Å in the Cu-chloride counterpart 3 (Fig.…”
Section: Resultsmentioning
confidence: 99%
“…The convenient and fast formation of isocyanide copper(I) complexes has been reported with three or four ligands around the metal center depending on the amount of added isocyanide. 38,39 During the synthesis, the corresponding tetrakis complexes must be obtained selectively as contamination with the tris complexes leads to insoluble polymeric materials during subsequent reactions.…”
Section: ■ Results and Discussionmentioning
confidence: 99%