543745-58-0Relevant articles and documents
Designing Homogeneous Bromine Redox Catalysis for Selective Aliphatic C?H Bond Functionalization
Becker, Peter,Duhamel, Thomas,Martínez, Claudio,Mu?iz, Kilian
supporting information, p. 5166 - 5170 (2018/03/28)
The potential of homogeneous oxidation catalysis employing bromine has remained largely unexplored. We herein show that the combination of a tetraalkylammonium bromide and meta-chloroperbenzoic acid offers a unique catalyst system for the convenient and s
Optimised conditions for styrene syntheses using Suzuki-Miyaura couplings and catalyst-ligand-base pre-mixes
Henderson, Laura,Knight, David W.,Rutkowski, Piotr,Williams, Andrew C.
, p. 4654 - 4656 (2012/09/05)
Optimised conditions are reported for Suzuki-Miyaura couplings between N-tosyl-2-bromo-benzylamines and -phenethylamines with vinylboronic acids, using pre-mixes of catalyst, ligand and base, leading to the corresponding 2-tosylaminomethyl- and 2-tosylami
A general approach to N-heterocyclic scaffolds using domino Heck-aza-Michael reactions
Priebbenow, Daniel L.,Stewart, Scott G.,Pfeffer, Frederick M.
supporting information; experimental part, p. 1508 - 1515 (2011/04/18)
Palladium-catalyzed domino Heck-aza-Michael reactions for the synthesis of a series of C1-substituted tetrahydro-β-carbolines, tetrahydroisoquinolines and isoindolines are described. The domino process involves the initial intermolecular Heck reaction of
A one-pot, three-component approach to functionalised tetrahydroisoquinolines using domino Heck-aza-Michael reactions
Priebbenow, Daniel L.,Pfeffer, Frederick M.,Stewart, Scott G.
supporting information; experimental part, p. 1632 - 1635 (2011/05/04)
A one-pot, three-component method incorporating a domino Heck-aza-Michael reaction has been developed for the rapid synthesis of functionalised tetrahydroisoquinolines. Following the in situ generation of an acrylamide, a domino process involving intermol
Pyrrolidine and piperidine formation via copper(II) carboxylate-promoted intramolecular carboamination of unactivated olefins: Diastereoselectivity and mechanism
Sherman, Eric S.,Fuller, Peter H.,Kasi, Dhanalakshmi,Chemler, Sherry R.
, p. 3896 - 3905 (2008/02/01)
(Chemical Equation Presented) An expanded substrate scope and in-depth analysis of the reaction mechanism of the copper(II) carboxylate-promoted intramolecular carboamination of unactivated alkenes is described. This method provides access to N-functionalized pyrrolidines and piperidines. Both aromatic and aliphatic γ- and δ-alkenyl N-arylsulfonamides undergo the oxidative cyclization reaction efficiently. N-Benzoyl-2-allylaniline also underwent the oxidative cyclization. The terminal olefin substrates examined were more reactive than those with internal olefins, and the latter terminated in elimination rather than carbon-carbon bond formation. The efficiency of the reaction was enhanced by the use of more organic soluble copper(II) carboxylate salts, copper(II) neodecanoate in particular. The reaction times were reduced by the use of microwave heating. High levels of diastereoselectivity were observed in the synthesis of 2,5-disubstituted pyrrolidines, wherein the cis substitution pattern predominates. The mechanism of the reaction is discussed in the context of the observed reactivity and in comparison to analogous reactions promoted by other reagents and conditions. Our evidence supports a mechanism wherein the N-C bond is formed via intramolecular syn aminocupration and the C-C bond is formed via intramolecular addition of a primary carbon radical to an aromatic ring.
Intramolecular palladium-catalyzed aryl amination and aryl amidation
Wolfe, John P.,Rennels, Roger A.,Buchwald, Stephen L.
, p. 7525 - 7546 (2007/10/03)
Upon treatment with a palladium catalyst and a suitable base, aromatic halides undergo intramolecular substitution to form five, six, and seven-membered rings. In a similar fashion aryl halides with pendant amides or sulfonamides are cyclized to form five and six-membered rings.
