115984-41-3Relevant academic research and scientific papers
Photoinduced Intermolecular [4+2] Cycloaddition Reaction for Construction of Benzobicyclo[2.2.2]octane Skeletons
Liu, Qiang,Wang, Junlei,Li, Dazhi,Yang, Chao,Xia, Wujiong
, p. 1389 - 1402 (2017/02/10)
A novel and efficient method for the synthesis of highly substituted benzobicyclo[2.2.2]octane skeletons has been explored. Under UV-light irradiation, o-divinylbenzenes underwent a pericyclic reaction to form the cyclic o-quinodimethane intermediates which were subsequently reacted with olefins through [4+2] addition to construct the benzobicyclo[2.2.2]octane skeletons in mild conditions. Gram scale reactions demonstrated the synthetic potential application of this protocol.
Synthesis of Oxatricyclooctanes via Photoinduced Intramolecular Oxa-[4+2] Cycloaddition of Substituted o-Divinylbenzenes
Liu, Qiang,Wang, Junlei,Li, Dazhi,Gao, Guo-Lin,Yang, Chao,Gao, Yuan,Xia, Wujiong
, p. 7856 - 7868 (2017/08/14)
The photolysis of substituted o-divinylbenzenes promotes a one-step and metal-free conversion to oxatricycles at room temperature. Irradiation o-divinylbenzenes results in an pericyclic reaction to form cyclic o-quinodiemthane intermediates, which subsequently undergo intramolecular oxa-[4+2] cycloaddition to form oxacyclic derivatives.
Selective arene functionalization through sequential oxidative and non-oxidative Heck reactions
Schmidt, Bernd,Elizarov, Nelli
, p. 4350 - 4352 (2012/06/04)
A sequence of acetamide directed oxidative Heck reaction and deacetylation-diazotation-Heck coupling allows the traceless removal of the acetamide group and its dual exploitation as a catalyst directing group and a leaving group. The Royal Society of Chem
Enantioselective copper-catalyzed reductive michael cyclizations
Oswald, Claire L.,Peterson, Justine A.,Lam, Hon Wal
supporting information; experimental part, p. 4504 - 4507 (2009/12/07)
In the presence of siloxanes as stoichiometric reductants, chiral copper-bisphosphine complexes catalyze highly enantioselective reductive Michael cyclizations of substrates containing two α,β-unsaturated carbonyl moieties. The diastereochemical outcome of these reactions Is dependent upon whether biaryl- or ferrocene-based chiral bisphosphines are employed.
Stereoselective RhI-catalyzed tandem conjugate addition of boronic acids-Michael cyclization
Navarro, Cristina,Csaky, Aurelio G.
, p. 217 - 219 (2008/09/18)
(Chemical Equation Presented) The first examples of the stereoselective sequence RhI-cataiyzed tandem conjugate addition of boronic acids to enones-Michael cyclization, is reported. The reaction is carried out in dioxane-H2O at rt, and 1,2,3-trisubstituted indans are obtained in a highly regio- and stereoselective fashion.
Tandem Michael/Michael reactions mediated by phosphines or aryl thiolates
Brown, Paul M.,K?ppel, Nina,Murphy, Patrick J.,Coles, Simon J.,Hursthouse, Michael B.
, p. 1100 - 1106 (2007/10/03)
Tri-n-butyl phosphine was found to effect tandem Michael/Michael cyclisations leading to the formation of cyclopentenes and cyclohexenes in good yields, whilst p-TolSH in conjunction with a catalytic amount of p-TolSNa effected cyclisation to the correspo
Oxime-Derived Palladium Complexes as Very Efficient Catalysts for the Heck-Mizoroki Reaction
Alonso, Diego A.,Najera, Carmen,Pacheco, Ma. Carmen
, p. 172 - 183 (2007/10/03)
Oxime-derived, chloro-bridged palladacycles 16 are efficient complexes for the Heck vinylation of aryl halides. The isolated catalysts are thermally stable, not sensitive to air or moisture and easily accessible from inexpensive starting materials. The reaction can be performed under aerobic conditions, with aryl iodides, bromides and chlorides with acrylic esters and olefins displaying turnover numbers (TON) of up to 1010 for phenyl iodide and turnover frequencies (TOF) of 1.4 × 108 h-1. Deactivated aryl bromides undergo the Heck reaction with styrene with TON and TOF values up to 97,000 and 6063 h-1, respectively. Even aryl chlorides undergo the coupling reaction with olefins with TON up to 920. Complexes 16 catalyze the synthesis of 2,3-disubstituted indenones and indoles in good yields via annulation reaction of internal alkynes with o-bromoor o-chlorobenzaldehyde and o-iodoaniline, respectively.
Tandem Michael/Michael reactions mediated by phosphines or aryl thiolates
Brown, Paul M,K?ppel, Nina,Murphy, Patrick J
, p. 8707 - 8710 (2007/10/03)
tri-n-Butyl phosphine was found to effect tandem Michael/Michael cyclisations leading to the formation of cyclopentenes and cyclohexenes in good yields, whilst p-TolSH in conjunction with a catalytic amount of p-TolSNa effected cyclisation to the correspo
A tellurium-triggered domino reaction for the synthesis of a 1-substituted-3-vinyl-1,3-dihydroisobenzofuran
Chao,Dittmer
, p. 6001 - 6004 (2007/10/03)
Telluride ion reacts with an oxiranemethanol toluenesulfonate in toluene under phase-transfer conditions to give an allylic alkoxide anion that is trapped by addition to an adjacent α,β-unsaturated ester to yield a furan derivative. Use of a non-racemic oxiranemethanol tosylate gives two furan diastereomers in a ratio of 56:44. (C) 2000 Elsevier Science Ltd.
Novel nine-membered titanaheterocycles - Structure, ab initio calculations, and preparative use towards the selective synthesis of substituted cyclopentanols
Hampel, Frank,Van Eikema Hommes, Nico,Hoops, Sven,Maaref, Faramarz,Schobert, Rainer
, p. 1253 - 1262 (2007/10/03)
Reactions of Cp2Ti(CO)2 (3) with two equivalents of α,β-unsaturated ketones 4 yield the novel titana-2,9-dioxacyclonona-3,7-dienes 5. Cross-coupling of 3 with two different ketones 4 and 6 to give 7 can be achieved under certain reaction conditions. Hydrolysis of 5 or 7 may generate diketones 9, cyclopentanols 10/11, or cyclopentenes 12/13, depending on substituents and conditions. The X-ray crystal structure of 5a, the first nine-membered bis(η5-cyclopentadienyl)-substituted titanaheterocycle containing carbon, is presented. Ab initio calculations were performed for 5a and for titana-2-oxacyclopentene 1, a conceivable intermediate in the coupling reaction.
