Copper/silver-cocatalyzed Conia-ene reactions of 2-alkynic 1,3-dicarbonyl compounds.
A copper/silver-catalyzed Conia-ene reaction has been developed for selectively constructing five-membered and six-membered rings. In the presence of (CuOTf)(2) x C(6)H(6) and AgBF(4), a variety of 2-alkynic 1,3-dicarbonyl compounds underwent the Conia-ene intramolecular reaction smoothly in moderate to good yields. It is noteworthy that both 2-phenylacetylhept-6-ynenitrile and diethyl 2-(pent-4-ynyl)malonate are also suitable substrates under the standard conditions, and the selectivity toward endo- or exo-products depends on the substituents at the terminal of alkynes.
Deng
Chen-Liang
CL
Key Laboratory of Chemical Biology & Traditional Chinese Medicine Research (Ministry of Education), Hunan Normal University, Changsha 410081, China.
Zou
Tao
T
Wang
Zhi-Qiang
ZQ
Song
Ren-Jie
RJ
Li
Jin-Heng
JH
D000480:Alkynes / Q000737:chemistry*; D002384:Catalysis; D003300:Copper / Q000737:chemistry*; D003500:Cyclization; D004952:Esters / Q000138:chemical synthesis / Q000737:chemistry; D007659:Ketones / Q000138:chemical synthesis / Q000737:chemistry*; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000737:chemistry*; D012834:Silver / Q000737:chemistry*; D013237:Stereoisomerism
D000480:Alkynes; D004952:Esters; D007659:Ketones; D009942:Organometallic Compounds; D012834:Silver; D003300:Copper