61967-54-2Relevant academic research and scientific papers
Dual Gold-Catalyzed Formal Tetradehydro-Diels–Alder Reactions for the Synthesis of Carbazoles and Indolines
Wang, Hong-Fa,Wang, Shi-Yue,Qin, Tian-Zhu,Zi, Weiwei
supporting information, p. 17911 - 17914 (2018/11/23)
This work reports a dual gold-catalyzed tetradehydro-Diels–Alder reaction for the synthesis of nitrogen-containing aromatic heterocycles. Under the catalytic system (IPrAuNTf2/DIPEA), indolines and carbazoles as well as other N-containing aromatic heterocycles were prepared in high yields with good functional group tolerance. Unlike the traditional thermal tetradehydro-Diels–Alder reactions, diluted reaction concentration and radical prohibitors are not required for this protocol. Experimental data support a mechanism involving gold vinylidene species, which undergoes a 6 π electrocyclization, followed with 1,2-hydrogen shift.
Isomerization of propargylic alcohols into α,β-unsaturated carbonyl compounds catalyzed by the sixteen-electron allyl-ruthenium(II) complex [Ru(η3-2-C3H4Me)(CO)(dppf)] [SbF 6]
Cadierno, Victorio,Garcia-Garrido, Sergio E.,Gimeno, Jose
, p. 101 - 110 (2007/10/03)
The 16-e- (η3-allyl)-ruthenium(II) complex [Ru(η3-2-C3H4Me)(CO)(dppf)][SbF 6] is an efficient catalyst for the regioselective isomerization of terminal propargylic alcohols HC≡CCR1R2(OH) into α,β-unsaturated aldehydes R1R2C=CHCHO or ketones R3R4C=C(R1)COMe (if R2 = CHR3R4) under mild conditions. This complex has been also used as catalyst for the preparation of conjugated 1,3-enynes via dehydration of propargylic alcohols.
Carbonylation of Alkynyl Epoxides: Synthesis of 5-Hydroxy-2,3-dienoate Esters and 2,3-Dihydrofuran-3-ol Derivatives
Piotti, Marcelo E.,Alper, Howard
, p. 8484 - 8489 (2007/10/03)
The carbonylation of alkynyl oxiranes catalyzed by (MePh2)4Pd in the presence of 20 atm of carbon monoxide in methanol gives methyl 5-hydroxy-2,3-pentadienoates in good yields. When the reaction is performed on alkynyl oxiranemethano
Synthetic and Kinetic Studies of the Intramolecular Diels-Alder Reactions of Cycloalkenylallenylphosphine Oxides
Curtin, Michael L.,Okamura, William H.
, p. 5278 - 5287 (2007/10/02)
Kinetic investigations reveal that diphenylphosphinoyl (diphenylphosphine oxide) substituted cycloalkenylallenes 13b-d undergo intramolecular Diels-Alder (IMDA) cyclizations at room temperature to afford adducts with gem-dialkyl effect accelerations of 4.
