36884-77-2Relevant academic research and scientific papers
Catalytic olefin hydroamination with aminium radical cations: A photoredox method for direct C-N bond formation
Musacchio, Andrew J.,Nguyen, Lucas Q.,Beard, G. Hudson,Knowles, Robert R.
supporting information, p. 12217 - 12220 (2014/12/09)
While olefin amination with aminium radical cations is a classical method for C-N bond formation, catalytic variants that utilize simple 2° amine precursors remain largely undeveloped. Herein we report a new visible-light photoredox protocol for the intramolecular anti-Markovnikov hydroamination of aryl olefins that proceeds through catalytically generated aminium radical intermediates. Mechanistic studies are consistent with a process involving amine oxidation via electron transfer, turnover-limiting C-N bond formation, and a second electron transfer step to reduce a carbon-centered radical, rendering the overall process redox-neutral. A range of structurally diverse N-aryl heterocycles can be prepared in good to excellent yields under conditions significantly milder than those required by conventional aminium-based protocols.
Step-economical synthesis of taxol-like tricycles through a palladium-catalyzed domino reaction
Petrignet, Julien,Boudhar, Aicha,Blond, Gaelle,Suffert, Jean
, p. 3285 - 3289 (2011/05/16)
A quick and easy way to produce tricycles related to the core structure of taxanes has been achieved using a palladium-catalyzed domino reaction (see scheme, Bz=benzoyl). These studies have been performed with function-oriented synthesis in mind. An effic
Addition of ArSSAr to dienes via intramolecular C-C bond formation initiated by a catalytic amount of ArS+
Matsumoto, Kouichi,Fujie, Shunsuke,Suga, Seiji,Nokami, Toshiki,Yoshida, Jun-Ichi
supporting information; experimental part, p. 5448 - 5450 (2009/12/08)
A catalytic amount of electrochemically generated "ArS +" ("ArS+" = ArS(ArSSAr)+) initiates a cation chain reaction of dienes that involves the addition of ArSSAr associated with stereoselective intramolecular carbon-carbon bond formation, and the direct (in-cell) electrolysis of a mixture of a diene and ArSSAr with a catalytic amount of electricity also effectively initiates the reaction. The Royal Society of Chemistry 2009.
Thiol-catalyzed acyl radical cyclization of alkenals
Yoshikai, Kazuya,Hayama, Tomoharu,Nishimura, Katsumi,Yamada, Ken-Ichi,Tomioka, Kiyoshi
, p. 681 - 683 (2007/10/03)
(Chemical Equation Presented) Thiol-catalyzed direct generation of acyl radicals and their intramolecular addition to olefins of alkenals gave 2-substituted five- and six-membered cyclic ketones in reasonably good yields. The combination of odorless tert-dodecanthiol and AIBN or V-40 was the initiator of choice among surveyed radical generators for the cyclization of alkenals. Aldehydes having electron-deficient olefins cyclized more easily than those having unactivated olefins.
Facile synthesis of the fused 6-6-5 ring system containing chroman ring from 2-(1-hydroxy-5-alkenyl)phenol derivatives via intramolecular inverse- electron-demand diels-alder reaction
Shrestha, Kedar Shanker,Honda, Kiyoshi,Asami, Masatoshi,Inoue, Seiichi
, p. 73 - 83 (2007/10/03)
A simple and facile synthesis of the fused 6-6-5 ring system, i.e., 1,2,3,3a,4,9b-hexahydrocyclopenta[c][1]benzopyrans, was achieved through the intramolecular [4+2] cycloaddition of o-quinonemethides generated from 2-(1- hydroxy-5-alkenyl)phenol derivatives under acidic conditions. In general, cis-fused tricyclic compounds of 6-6-5 ring system were obtained as the major products. Reactivity and selectivity of the cycloaddition reaction depended on the substituents on the aromatic ring and in the dienophilic olefin moiety.
Intramolecular anodic olefin coupling reactions: A useful method for carbon-carbon bond formation
Hudson, Christine M.,Marzabadi, Mohammad R.,Moeller, Kevin D.,New, Dallas G.
, p. 7372 - 7385 (2007/10/02)
The utility of intramolecular anodic olefin coupling reactions for effecting carbon-carbon bond formation has been examined. All of the successful cyclizations studied utilized either an alkyl or silyl enol ether as one of the participating olefins. The e
KINETICALLY DISTINCT TRIPLETS IN THE PHOTOREARRANGEMENT OF 2-PHENYLCYCLOHEXANONE TO cis- AND trans-6-PHENYL-5-HEXENALS
Wagner, Peter J.,Stratton, Thomas J.
, p. 3317 - 3322 (2007/10/02)
A reinvestigation of the photochemistry of 2-phenylcyclohexanone reveals that the two aldehyde products, cis- and trans-6-phenyl-5-hexenal, come from triplets of different lifetimes.That the two distinct triplets are not simply the two conformers with phe
