87266-35-1Relevant academic research and scientific papers
Phosphabarrelene-modified Rh-catalysts: A new and selective route towards hydroxy-functionalized bicyclic imidazoles via tandem reactions
Baeuerlein, Patrick S.,Gonzalez, Ismael Arenas,Weemers, Jarno J. M.,Lutz, Martin,Spek, Anthony L.,Vogt, Dieter,Mueller, Christian
, p. 4944 - 4946 (2009)
8-Hydroxy-6-methyl-5,6,7,8-tetrahydroimidazo[1,2-a]pyridine was formed selectively in high yields from N-(β-methallyl)imidazole by a tandem hydroformylation-cyclization sequence, representing a novel one-pot catalytic synthesis of bicyclic imidazole deriv
Acceptorless Alcohol Dehydrogenation: OH vs NH Effect in Bifunctional NHC-Ir(III) Complexes
González Miera, Greco,Martínez-Castro, Elisa,Martín-Matute, Belén
supporting information, p. 636 - 644 (2018/03/21)
Bifunctional complexes bearing N-heterocyclic carbene (NHC) ligands functionalized with hydroxy or amine groups were synthesized to measure the beneficial effect of different modes of metal-ligand cooperation in the acceptorless dehydrogenation of alcohols. In comparison to complexes with an amine moiety, hydroxy-functionalized iridium catalysts showed superior activity. In contrast to alcohols, 1,4-diols underwent cyclization to give the corresponding tetrahydrofurans without involving dehydrogenation processes. Mechanistic investigations to rationalize the "OH effect" in these types of complexes have been undertaken.
Palladium-Catalyzed Dehydrative Cross-Coupling of Allylic Alcohols and N-Heterocycles Promoted by a Bicyclic Bridgehead Phosphoramidite Ligand and an Acid Additive
Kang, Kyungjun,Kim, Jaewook,Lee, Ansoo,Kim, Woo Youn,Kim, Hyunwoo
supporting information, p. 616 - 619 (2016/02/18)
A mild and efficient dehydrative cross-coupling reaction between allylic alcohols and N-heterocycles using palladium catalysis is reported. A bicyclic bridgehead phosphoramidite (briphos) ligand together with Pd(dba)2 is a highly efficient catalyst, and an acid additive involved in the rate-determining step promotes the catalytic cycle. The coupling reaction of allylic alcohols with N-heterocycles including imidazoles, benzimidazoles, and triazole proceeds under mild reaction conditions with high yields using Pd/briphos and pentafluorophenol.
N, N′-Olefin functionalized Bis-Imidazolium Pd(II) chloride N-Heterocyclic carbene complex builds a supramolecular framework and shows catalytic efficacy for 'C-C' coupling reactions
Roymahapatra, Gourisankar,Samanta, Tapastaru,Seth, Saikat Kumar,Mahapatra, Ambikesh,Chattopadhyay, Shyamal Kumar,Dinda, Joydev
, p. 1057 - 1065 (2015/09/07)
The ligand 3,3′-(p-phenylenedimethylene)bis{1-(2-methylallyl)} imidazolium bromide (1) and its Palladium(II) N-heterocyclic carbene (NHC) complex (3) has been synthesized and characterized by several spectroscopic techniques and the solid-state structure of 3 has been determined by single crystal X-ray diffraction studies. The Pd(II) complex possesses ring head to tail π- π stacking interactions (3.767 A ) through imidazole rings. Complex 3 catalyzes Suzuki-Miyaura 'C-C' coupling reaction. DFT calculations have been used to understand the HOMO/LUMO energy and hence the stability and reactivity of Pd(II) complex in syn and anti-configuration.
An improved and convenient procedure for the synthesis of 1-substituted imidazoles
Kamijo,Yamamoto,Harada,Iizuka
, p. 1213 - 1221 (2007/10/02)
1-Protected imidazoles, such as 1-acetyl- and 1-benzoylimidazoles, react with various halides, such as benzyl, allyl, α-keto, and alkyl halides, to give 1-protected-3-substituted imidazolium salts in high yields. The resultant imidazolium salts are easily deprotected by treatment with water or alcohols to give the corresponding 1-substituted imidazoles in excellent yields. In this reaction the yields of 1-substituted imidazoles vary with the kinds of halides used and/or with the protecting groups, and the yields increase in the following order: benzyl halides≥allyl halides~α-keto halides>alkyl halides, and acetyl≥benzoyl>ethoxycarbonyl>diethoxymethyl>trimethylsilyl>tosyl.
