19810-20-9Relevant academic research and scientific papers
Selective Hydroarylation of 1,3-Diynes Using a Dimeric Manganese Catalyst: Modular Synthesis of Z-Enynes
Yan, Zhongfei,Yuan, Xiang-Ai,Zhao, Yue,Zhu, Chengjian,Xie, Jin
supporting information, p. 12906 - 12910 (2018/09/25)
The transition-metal-catalyzed selective hydroarylation of unsymmetrical alkynes represents the state-of-art in organic chemistry, and still mainly relies on the use of precious late-transition-metal catalysts. Reported herein is an unprecedented MnI-catalyzed hydroarylation of unsymmetrical 1,3-diyne alcohols with commercially available arylboronic acids with predictive selectivity. This method addresses the challenges in regio-, stereo-, and chemoselectivity. It offers a general, convenient and practical strategy for the modular synthesis of multisubstituted Z-configurated conjugated enynes. This protocol is distinguished by its operational simplicity, complete selectivity, excellent functional-group compatibility, and gram-scale potential. A dimeric MnI species, Mn2(CO)8Br2, was proven to be a much more efficient catalyst precursor than Mn(CO)5Br.
Copper-Catalyzed Hydroarylation of Internal Alkynes: Highly Regio- and Diastereoselective Synthesis of 1,1-Diaryl, Trisubstituted Olefins
Kortman, Gregory D.,Hull, Kami L.
, p. 6220 - 6224 (2017/09/15)
The copper-catalyzed hydroarylation of internal, unsymmeric alkynes is presented. Trisubstituted alkenes are obtained as single diastereomers in good to excellent yields and excellent regioselectivities. The scope of the reaction is presented with respect to alkyne and aryl iodide coupling partners. Initial mechanistic experiments indicate a hydrocupration event followed by a two-electron oxidative addition/reductive elimination pathway.
Al(OTf)3: An efficient lewis acid additive for domino addition-elimination of Grignard reagents to activated ketones
Pieterse, Tanya,Visser, Melanie,Marais, Charlene,Bezuidenhoudt, Barend C. B.
supporting information, p. 1541 - 1546 (2016/06/14)
It has been demonstrated that aluminium triflate in either stoichiometric or catalytic quantities facilitates the addition-elimination of Grignard reagents to electron-rich ketones, such as methoxy substituted acetophenones, propiophenone and chromanone in a one-pot process, and that it has an enhancing effect on the addition of these reagents to the ketones. It has also been found that the reactions are highly stereoselective towards one regioisomer of the alkene in the case of oxygenated aryl-alkyl substituted substrates, but not when the elimination originates from a double benzylic alcohol intermediate.
Metal-free Mizoroki-Heck type reaction: A radical oxidative coupling reaction of 2-chloro-dithiane with substituted olefins
Du, Wenbin,Lai, Junshan,Tian, Lixia,Xie, Xingang,She, Xuegong,Tang, Shouchu
, p. 14017 - 14020 (2015/01/16)
An efficient metal-free Mizoroki-Heck type reaction of di- and tri-substituted alkenes with 2-chloro-dithiane has been developed under ambient pressure of air or using a relatively low loading of BF3·Et2O. This study represents a new environmentally friendly method for the syntheses of dithianyl-substituted alkene derivatives via a radical oxidative coupling process.
Palladium catalyzed coupling of tosylhydrazones with aryl and heteroaryl halides in the absence of external ligands: Synthesis of substituted olefins
Ojha, Devi Prasan,Prabhu, Kandikere Ramaiah
, p. 11027 - 11033 (2013/02/22)
Palladium catalyzed cross-coupling reaction of hydrazones with aryl halides in the absence of external ligand is reported. The versatility of this coupling reaction is demonstrated in showcasing the selectivity of coupling reaction in the presence of hydr
Microwave-assisted, Pd(0)-catalyzed cross-coupling of diazirines with aryl halides
Zhao, Xia,Wu, Guojiao,Yan, Chong,Lu, Kui,Li, Hui,Zhang, Yan,Wang, Jianbo
supporting information; experimental part, p. 5580 - 5583 (2011/02/23)
Pd(0)-catalyzed cross-coupling reactions of diazirines with aryl halides under microwave heating conditions afford a series of substituted olefins. A reaction mechanism involving the migratory insertion of the Pd carbene intermediate is proposed.
Friedel-Crafts alkenylation of arenes using alkynes catalysed by metal trifluoromethanesulfonates
Tsuchimoto,Maeda,Shirakawa,Kawakami
, p. 1573 - 1574 (2007/10/03)
Metal trifluoromethanesulfonates [M(OTf)(n); M = Sc, Zr, In] catalyse the Friedel-Crafts alkenylation of arenes using alkynes, including internal alkynes, to give, through an alkenyl cation intermediate, 1,1-diarylalkenes in high to excellent yields.
