title: One-pot synthesis of 2,5-dihydropyrroles from terminal alkynes, azides, and propargylic alcohols by relay actions of copper, rhodium, and gold.
abstract: Relay actions of copper, rhodium, and gold formulate a one-pot multistep pathway, which directly gives 2,5-dihydropyrroles starting from terminal alkynes, sulfonyl azides, and propargylic alcohols. Initially, copper-catalyzed 1,3-dipolar cycloaddition of terminal alkynes with sulfonyl azides affords 1-sulfonyl-1,2,3-triazoles, which then react with propargylic alcohols under the catalysis of rhodium. The resulting alkenyl propargyl ethers subsequently undergo the thermal Claisen rearrangement to give α-allenyl-α-amino ketones. Finally, a gold catalyst prompts 5-endo cyclization to produce 2,5-dihydropyrroles.
authors.affiliation: Department of Synthetic Chemistry and Biological Chemistry, Kyoto University, Katsura, Kyoto 615-8510 (Japan). tmiura@sbchem.kyoto-u.ac.jp.
authors.forename: Tomoya
authors.initials: T
authors.lastname: Miura
authors.forename: Takamasa
authors.initials: T
authors.lastname: Tanaka
authors.forename: Kohei
authors.initials: K
authors.lastname: Matsumoto
authors.forename: Masahiro
authors.initials: M
authors.lastname: Murakami
mesh_terms: D000480:Alkynes / Q000737:chemistry*; D001386:Azides / Q000737:chemistry*; D002384:Catalysis; D020650:Combinatorial Chemistry Techniques; D003300:Copper / Q000737:chemistry; D006046:Gold / Q000737:chemistry; D020005:Propanols / Q000737:chemistry*; D011758:Pyrroles / Q000138:chemical synthesis* / Q000737:chemistry; D012238:Rhodium / Q000737:chemistry; D014230:Triazoles / Q000737:chemistry
chemical_list: D000480:Alkynes; D001386:Azides; D020005:Propanols; D011758:Pyrroles; D014230:Triazoles; C013231:pyrroline; D006046:Gold; D003300:Copper; D012238:Rhodium; C028255:propargyl alcohol
keywords: copper; gold; rhodium; terminal alkynes; triazoles