3899-63-6Relevant academic research and scientific papers
Pd-Catalyzed Alkene Difunctionalization Reactions of Enolates for the Synthesis of Substituted Bicyclic Cyclopentanes
Bornowski, Evan C.,Hinds, Elsa M.,White, Derick R.,Nakamura, Yusuke,Wolfe, John P.
, p. 1610 - 1630 (2019)
Palladium-catalyzed alkene difunctionalization reactions between alkenes bearing tethered aryl or alkenyl triflates and enolate nucleophiles are described. The transformations form two C-C bonds, a ring, and up to two stereocenters while producing substit
Dual nickel and Lewis acid catalysis for cross-electrophile coupling: The allylation of aryl halides with allylic alcohols
Jia, Xue-Gong,Guo, Peng,Duan, Jicheng,Shu, Xing-Zhong
, p. 640 - 645 (2018/01/28)
Controlling the selectivity in cross-electrophile coupling reactions is a significant challenge, particularly when one electrophile is much more reactive. We report a general and practical strategy to address this problem in the reaction between reactive and unreactive electrophiles by a combination of nickel and Lewis acid catalysis. This strategy is used for the coupling of aryl halides with allylic alcohols to form linear allylarenes selectively. The reaction tolerates a wide range of functional groups (e.g. silanes, boronates, anilines, esters, alcohols, and various heterocycles) and works with various allylic alcohols. Complementary to most current routes for the C3 allylation of an unprotected indole, this method provides access to C2 and C4-C7 allylated indoles. Preliminary mechanistic experiments reveal that the reaction might start with an aryl nickel intermediate, which then reacts with Lewis acid activated allylic alcohols in the presence of Mn.
Synthesis of Functionalized Benzo[b]furans via Oxidative Cyclization of o-Cinnamyl Phenols
Rehan, Mohammad,Nallagonda, Rajender,Das, Braja Gopal,Meena, Tannu,Ghorai, Prasanta
supporting information, p. 3411 - 3424 (2017/04/13)
Disclosed herein is an efficient synthetic route for the synthesis of functionalized 2-benzyl benzo[b]furans via a regioselective 5-exo-trig intramolecular oxidative cyclization of ortho-cinnamyl phenols using [PdCl2(CH3CN)2] as catalyst and benzoquinone as an oxidant. Further, a sequential ortho-cinnamylation of phenols using cinnamyl alcohols catalyzed by Re2O7, followed by an oxidative cyclization using the above Pd catalyst, is performed. The reaction showed broad substrate scope with good to excellent yields.
Synthesis of chromans via [3 + 3] cyclocoupling of phenols with allylic alcohols using a Mo/o-chloranil catalyst system
Yamamoto, Yoshihiko,Itonaga, Kouhei
supporting information; experimental part, p. 717 - 720 (2009/08/19)
(Chemical Equation Presented) The combination of a molybdenum complex (CpMoCl(CO)3 or [CpMo(CO)3]2) and o-chloranil was used as a catalyst in the [3 + 3] cyclocoupling of phenols and allylic alcohols under microwave heating conditions. Substituted chromans were selectively obtained in moderate to good isolated yields.
