445235-57-4Relevant academic research and scientific papers
Experimental and Computational Studies of Palladium-Catalyzed Spirocyclization via a Narasaka-Heck/C(sp3or sp2)-H Activation Cascade Reaction
Wei, Wan-Xu,Li, Yuke,Wen, Ya-Ting,Li, Ming,Li, Xue-Song,Wang, Cui-Tian,Liu, Hong-Chao,Xia, Yu,Zhang, Bo-Sheng,Jiao, Rui-Qiang,Liang, Yong-Min
supporting information, p. 7868 - 7875 (2021/05/27)
The first synthesis of highly strained spirocyclobutane-pyrrolines via a palladium-catalyzed tandem Narasaka-Heck/C(sp3 or sp2)-H activation reaction is reported here. The key step in this transformation is the activation of a δ-C-H bond via an in situ generated σ-alkyl-Pd(II) species to form a five-membered spiro-palladacycle intermediate. The concerted metalation-deprotonation (CMD) process, rate-determining step, and energy barrier of the entire reaction were explored by density functional theory (DFT) calculations. Moreover, a series of control experiments was conducted to probe the rate-determining step and reversibility of the C(sp3)-H activation step.
Highly Enantioselective Iridium-Catalyzed Hydrogenation of 2-Aryl Allyl Phthalimides
Cabré, Albert,Romagnoli, Elia,Martínez-Balart, Pol,Verdaguer, Xavier,Riera, Antoni
supporting information, p. 9709 - 9713 (2019/11/19)
The iridium-catalyzed asymmetric hydrogenation of 2-aryl allyl phthalimides to afford enantioenriched β-aryl-β-methyl amines is presented. Recently developed Ir-MaxPHOX catalysts are used for this enantioselective transformation. The mild reaction conditions and the feasible removal of the phthalimido group makes this catalytic method easily scalable and of great interest to afford chiral amines. The importance of this new methodology is exemplified by the formal synthesis of (R)-Lorcaserin, OTS514, and enantiomerically enriched 3-methyl indolines.
Synthesis of 2,5-Diaryl-1,5-dienes from Allylic Bromides Using Visible-Light Photoredox Catalysis
Pratsch, Gerald,Overman, Larry E.
, p. 11388 - 11397 (2015/12/01)
Visible-light photoreductive coupling of 2-arylallyl bromides in the presence of the photocatalyst Ru(bpy)3(PF6)2, a Hantzsch ester, and i-Pr2NEt gives 2,5-diaryl-1,5-dienes in high yield. This method avoids the use of stoichiometric metal reductants and is compatible with the presence of halogen, alkyl, electron-donating, and electron-withdrawing substituents on the aromatic ring.
Catalytic enantioselective iodoaminocyclization of hydrazones
Tripathi, Chandra Bhushan,Mukherjee, Santanu
supporting information, p. 3368 - 3371 (2014/07/08)
The first catalytic enantioselective iodoaminocyclization of β,γ-unsaturated hydrazones has been developed with the help of a trans-1,2-diaminocyclohexane-derived bifunctional thiourea catalyst and allows for the direct access to δ2-pyrazolines containing a quaternary stereogenic center in high yield with good enantioselectivity (up to 95% yield and 95:5 er).
Catalytic enantioselective iodoetherification of oximes
Tripathi, Chandra Bhushan,Mukherjee, Santanu
supporting information, p. 8450 - 8453 (2013/09/02)
Organocatalysis: The first catalytic enantioselective iodoetherification of oximes is developed using commercially available N-iodosuccinimide. In the presence of a dihydrocinchonidine-derived thiourea (10 mol %), β,γ-unsaturated oximes undergo facile iodoetherification to produce Δ2-isoxazolines containing a quaternary stereogenic center generally in high yield with good to excellent enantioselectivity. Copyright
An intriguing effect of Yb(OTf)3-TMSCl in the halogenation of 1,1-disubstituted alkenes by NXS: Selective synthesis of allyl halides
Yamanaka, Masamichi,Arisawa, Mitsuhiro,Nishida, Atsushi,Nakagawa, Masako
, p. 2403 - 2406 (2007/10/03)
A novel protocol to effect the efficient selective halogenation of 1,1-disubstituted alkenes with NXS catalyzed by Yb(OTf)3-TMSCl, which affords the corresponding allyl halides in high yield, including allyl bromide, chloride, iodide and fluori
