437611-92-2Relevant academic research and scientific papers
Synthesis of chiral tetrasubstituted alkenes by an asymmetric cascade reaction catalyzed cooperatively by cationic rhodium(I) and silver(I) complexes
Daiki, Hojo,Noguchi, Keiichi,Tanaka, Ken
, p. 8129 - 8132 (2009)
Fantastic four: Tetrasubstituted alkenes have been prepared with high enantioselectivity by the title transformation. This reaction was successfully applied to the enantio- and diastereoselective synthesis of tetrasubstituted helical alkenes possessing bo
Palladium-Catalyzed Aminomethylative Oppolzer-Type Cyclization of Enynes: Access to Aminomethylated Benzofulvenes
Huang, Hanmin,Huang, Renbin,Li, Renren,Yu, Bangkui
, p. 9510 - 9515 (2021/12/14)
A novel palladium-catalyzed Oppolzer-type cyclization reaction aided by the aminomethyl cyclopalladated complex has been developed, which provides rapid access to functionalized benzofulvenes with excellent stereoselectivity. The corresponding products can undergo Diels–Alder reaction with maleimides, providing a series of complex polycyclic compounds with excellent regio- and stereoselectivities.
Design and Synthesis of Fused Pyridine Building Blocks for Automated Library Generation
Mora-Radó, Helena,Czechtizky, Werngard,Méndez, María,Harrity, Joseph P. A.
supporting information, p. 328 - 334 (2020/12/17)
We demonstrate that a diboration-electrocyclization sequence provides access to a range of pyridine-fused, small-molecule boronic ester building blocks, and that these are amenable to high-throughput synthesis leading to biaryl and ether-linked compound libraries. Moreover, the implementation of an integrated physicochemical and ADME profiling workflow allows accelerated design of novel lead compounds for application in drug-discovery projects.
Palladium-catalyzed chemoselective aminomethylative cyclization and aromatizing allylic amination: Access to functionalized naphthalenes
Yu, Bangkui,Yu, Houjian,Huang, Hanmin
, p. 8962 - 8966 (2020/11/13)
A palladium-catalyzed chemoselective aminomethylative cyclization and aromatizing allylic amination of enyne-tethered allylic alcohols with aminals is described. Under the reaction conditions, the cationic vinyl allylpalladium species undergoes selective migratory insertion of alkenes rather than reductive elimination with nucleophiles. This strategy provides an efficient and unique approach to the construction of functionalized naphthalenes, which are important building blocks in synthetic organic chemistry. Mechanistic studies have revealed that the selective sequential migratory insertion of enyne and alkene is crucial for the cyclization.
Cu(i)-Catalyzed addition-cycloisomerization difunctionalization reaction of 1,3-enyne-alkylidenecyclopropanes (ACPs)
Li, Peng-Hua,Wei, Yin,Shi, Min
, p. 7127 - 7138 (2020/10/06)
A copper(i)-catalyzed three-component addition-cycloisomerization difunctionalization reaction of 1,3-enyne-ACPs with Togni I reagent and TMSCN under mild reaction conditions has been developed, affording 3-trifluoroethylcyclopenta[b]naphthalene-4-carbonitrile derivatives. The reaction proceeded through a copper(i)-catalyzed 1,4-addition of conjugated 1,3-enynes via a radical relay process and aromatic cycloisomerization of allene-ACP intermediates.
An Alkyne Diboration/6π-Electrocyclization Strategy for the Synthesis of Pyridine Boronic Acid Derivatives
Mora-Radó, Helena,Bialy, Laurent,Czechtizky, Werngard,Méndez, María,Harrity, Joseph P. A.
supporting information, p. 5834 - 5836 (2016/05/09)
A new and efficient synthesis of pyridine-based heteroaromatic boronic acid derivatives is reported through a novel diboration/6π-electrocyclization strategy. This method delivers a range of functionalized heterocycles from readily available starting materials.
Novel platinum-catalyzed tandem reaction: An efficient approach to construct naphtho[l,2-b]furan
Wei, Hao,Zhai, Hongbin,Xu, Peng-Fei
supporting information; experimental part, p. 2224 - 2226 (2009/07/01)
An efficient approach to synthesize naphtho[1,2-b]furan has been developed via platinum-catalyzed tandem reaction. This new tandem catalysis induces a cycloisomerization of allenyl ketone, followed by a 6Π-electrocyclization- type reaction of carbene intermediate. The metal carbene proved to be an effective intermediate in the 6π-electrocyclization-type reaction.
Synthesis of substituted isoquinolines by electrophilic cyclization of iminoalkynes
Huang, Qinhua,Hunter, Jack A.,Larock, Richard C.
, p. 3437 - 3444 (2007/10/03)
The tert-butylimines of o-(1-alkynyl)benzaldehydes and analogous pyridinecarbaldehydes have been cyclized under very mild reaction conditions in the presence of I2, ICl, PhSeCl, PhSCl, and p-O2-NC6H4SCl to give the corresponding halogen-, selenium-, and sulfur-containing disubstituted isoquinolines and naphthyridines, respectively. This methodology accommodates a variety of iminoalkynes and affords the anticipated heterocycles in moderate to excellent yields. Monosubstituted isoquinolines and naphthyridines have been synthesized by the metal-catalyzed ring closure of these same iminoalkynes. The silver-catalyzed ring closure is highly effective in cyclizing aryl-, alkenyl-, and alkyl-substituted iminoalkynes at 50°C.
