174666-19-4Relevant academic research and scientific papers
Palladium-Catalyzed Cross-Coupling of Silyl Electrophiles with Alkylzinc Halides: A Silyl-Negishi Reaction
Cinderella, Andrew P.,Vulovic, Bojan,Watson, Donald A.
supporting information, p. 7741 - 7744 (2017/06/21)
We report the first example of a silyl-Negishi reaction between secondary zinc organometallics and silicon electrophiles. This palladium-catalyzed process provides direct access to alkyl silanes. The delicate balance of steric and electronic parameters of the employed DrewPhos ligand is paramount to suppressing isomerization and promoting efficient and selective cross-coupling.
Highly nucleophilic Vitamin B12-assisted nickel-catalysed reductive coupling of aryl halides and non-activated alkyl tosylates
Komeyama, Kimihiro,Ohata, Ryo,Kiguchi, Shinnosuke,Osaka, Itaru
supporting information, p. 6401 - 6404 (2017/07/10)
Reductive cross-coupling of aryl halides with ubiquitous alkyl tosylates was developed using a combination of nickel and vitamin B12 (VB12: cyanocobalamin) catalysts. The tosylate was activated by reduced VB12 to form alkyl cobalt(iii), which served as a good alkylating agent for aryl-nickel species, leading to C(sp3)-C(sp2) bond formation.
Synthesis of α-Tertiary Amine Derivatives by Intermolecular Hydroamination of Unfunctionalized Alkenes with Sulfamates under Trifluoromethanesulfonic Acid Catalysis
Fei, Jun,Wang, Zhen,Cai, Zheren,Sun, Hao,Cheng, Xu
supporting information, p. 4063 - 4068 (2016/01/25)
An efficient and mild trifluoromethanesulfonic acid-catalyzed hydroamination of unfunctionalized alkenes to afford α-tertiary amine derivatives at temperatures as low as room temperature is reported. 2,2,2-Trifluoroethyl sulfamate was found to be the optimal nitrogen source because its good solubility in both organic solvents and water facilitated both conversion and purification. The reaction conditions were compatible with a variety of substrate functional groups and afforded moderate to good yields. The desired amine compounds could be obtained easily by means of a mild, one-pot, redox-neutral deprotection procedure. Caryolane amine was synthesized with excellent chemo- and regioselectivities by means of a cascade hydroamination reaction of β-caryophyllene.
Redox chain reaction - Indole and pyrrole alkylation with unactivated secondary alcohols
Han, Xinping,Wu, Jimmy
supporting information, p. 4637 - 4640 (2013/05/22)
Secondary role: Indole and pyrrole derivatives are alkylated with unactivated secondary aliphatic alcohols by a Bronsted acid-catalyzed redox chain reaction mechanism. Broad functional-group tolerance has been demonstrated and preliminary studies suggest that 1,4-reduction of a putative indolyl carbocation is the dominant mechanistic pathway. Copyright
Direct cobalt-catalyzed conjugate addition of functionalized aryl halides and triflates: A new strategy for the conjugate addition onto methyl vinyl ketone
Amatore, Muriel,Gosmini, Corinne
experimental part, p. 1073 - 1076 (2009/10/10)
An efficient cobalt-catalyzed method for the direct conjugate addition of functionalized aryl halides or triflates onto methyl vinyl ketone is described. The experimentally simple procedure relies on the use of a catalytic system consisting of CoBr2(Bpy) and zinc and does not require the preformation of a stoichiometric organometallic species. The approach described herein displays considerable functional-group compatibility at good to excellent yields. Georg Thieme Verlag Stuttgart.
CoBr2(Bpy): An efficient catalyst for the direct conjugate addition of aryl halides or triflates onto activated olefins
Amatore, Muriel,Gosmini, Corinne,Perichon, Jacques
, p. 6130 - 6134 (2007/10/03)
An efficient cobalt-catalyzed method devoted to the direct conjugate addition of functionalized aryl compounds onto Michael acceptors is described. The CoBr2(2,2′-bipyridine) complex appears to be an extremely suitable catalyst for the activation of a variety of aromatic reagents ranging from halides to triflates functionalized by reactive groups. This procedure allows for the synthesis of compounds resulting from 1,4-addition in good to excellent yields. The versatility of this original process represents a simple alternative to most known methods using organometallic reagents.
Nickel-catalyzed electrochemical arylation of activated olefins
Condon, Sylvie,Dupre, Daniel,Falgayrac, Gilles,Nedelec, Jean-Yves
, p. 105 - 111 (2007/10/03)
Nickel-catalyzed electrochemical conjugate additions of substituted aryl bromides to activated olefins under recently optimized reaction conditions are reported. Good to high yields were obtained, whatever the nature of substituents in the meta- and para-positions of the benzene ring. In the ortho-substituted series, yields were good with electron-donating substituents, but low with electron-withdrawing groups. The activation of aryl chlorides and the sequential functionalization of aryl dihalides were also investigated.
Addition of electrochemically prepared arylzinc species onto activated olefins via a cobalt catalysis
Gomes, Paulo,Gosmini, Corinne,Périchon, Jacques
, p. 1673 - 1676 (2007/10/03)
The consumable anode process allows the electrochemical preparation of arylzinc compounds in the presence of cobalt chloride as catalyst in a mixed solvent acetonitrile/pyridine (9:1). Conjugate addition of these organometallic reagents to olefins is also obtained in good yields via a new method using CoBr2(2,2′-bipyridine)2 as catalyst.
Nonpeptide α(v)β3 antagonists. 1. Transformation of a potent, integrin-selective α(IIb)β3 antagonist into a potent α(v)β3 antagonist
Duggan,Duong,Fisher,Hamill,Hoffman,Huff,Ihle,Leu,Nagy,Perkins,Rodan,Wesolowski,Whitman,Zartman,Rodan,Hartman
, p. 3736 - 3745 (2007/10/03)
Modification of the potent fibrinogen receptor (α(IIb)β3) antagonist 1 generated compounds with high affinity for the vitronectin receptor α(v)β3. Sequential modification of the basic N-terminus of 1 led to the identification of the
Cobalt bromide as catalyst in electrochemical addition of aryl halides onto activated olefins
Gomes, Paulo,Gosmini, Corinne,Nédélec, Jean-Yves,Périchon, Jacques
, p. 3385 - 3388 (2007/10/03)
The consumable anode process permits the electrochemical arylation of activated olefins from functionalized aryl halides when cobalt halide is used as catalyst, either associated with bipyridine and pyridine as ligands in DMF as solvent, or with only pyridine in acetonitrile as solvent. (C) 2000 Published by Elsevier Science Ltd.
