53916-68-0Relevant academic research and scientific papers
Palladium-Catalyzed Stereoselective Aza-Wacker-Heck Cyclization: One-Pot Stepwise Strategy toward Tetracyclic Fused Heterocycles
Chen, Li-Yuan,Chuang, Ta-Hsien,Lai, Chin-Hung,Tang, Rong-Shiow
, p. 9337 - 9341 (2020/12/21)
Palladium-catalyzed intramolecular tandem cyclization reactions were conducted for the synthesis of densely cis/cis-fused aza-tetracyclic structures. The process involved a palladium(II)-catalyzed aerobic aza-Wacker reaction, followed by a palladium(0)-catalyzed Heck reaction. The effects of the solvent and benzene substitution pattern on the one-pot, two-step cascade reaction were studied systematically, and a probable mechanism was proposed. Strained pentahydrobenzo[f]cyclopenta[hi]indolizin-6-one and racemic γ-lycorane can also be synthesized rapidly using this palladium-catalyzed aza-Wacker-Heck cyclization reaction.
Palladium-Catalyzed Regioselective C-H Iodination of Unactivated Alkenes
Schreib, Benedikt S.,Carreira, Erick M.
, p. 8758 - 8763 (2019/06/13)
A palladium-catalyzed C-H iodination of unactivated alkenes is reported. A picolinamide directing group enables the regioselective functionalization of a wide array of olefins to furnish iodination products as single stereoisomers. Mechanistic investigations suggest the reversible formation of a six-membered alkenyl palladacycle intermediate through a turnover-limiting C-H activation.
Palladium-Catalyzed Aerobic Oxidative Cyclization of Aliphatic Alkenyl Amides for the Construction of Pyrrolizidine and Indolizidine Derivatives
Lo, Kai-Yip,Ye, Liu,Yang, Dan
, p. 1570 - 1575 (2017/08/11)
An efficient palladium-catalyzed aerobic oxidative cyclization has been developed to synthesize a variety of pyrrolizidine and indolizidine derivatives from simple aliphatic alkenyl amides in moderate to good yields. The reaction features the capability of accessing various N-heterocycles and the use of molecular oxygen (1 atm) as the green oxidant.
Visible-light-promoted selenofunctionalization of alkenes
Conner, Elizabeth S.,Crocker, Katherine E.,Fernando, Ranelka G.,Fronczek, Frank R.,Stanley, George G.,Ragains, Justin R.
supporting information, p. 5558 - 5561 (2013/11/19)
A visible-light-promoted method for the selenofunctionalization (and tellurofunctionalization) of alkenes has been developed. This method obviates the prepreparation of moisture-sensitive chalcogen electrophiles. The experimental setup is simple, and supe
Metal-free oxidative cyclization of urea-tethered alkenes with hypervalent iodine
Cochran, Brian M.,Michael, Forrest E.
supporting information; experimental part, p. 5039 - 5042 (2009/05/31)
(Chemical Equation Presented) A metal-free oxidative cyclization of ureas onto unactivated alkenes using iodosylbenzene and an acid promoter is described. The products isolated are predominantly bicyclic isoureas resulting from an intramolecular oxyamination reaction. The acid type and urea substitution have a strong effect on the product formed. A variety of substrates form the isourea with high diastereoselectivity via syn addition including di- and trisubstituted alkenes. Hydrolysis of the isourea gives access to new diastereomerically pure prolinol derivatives.
