13436-48-1Relevant articles and documents
Pd-Catalyzed C-H Annulation of Five-Membered Heteroaryl Halides with Norbornene Derivatives
Padhi, Birakishore,Kang, Geunhee,Kim, Eunmin,Ha, Jeongmin,Kim, Hyun Tae,Lim, Jeewoo,Joo, Jung Min
, p. 1792 - 1798 (2020)
Complementary to Catellani-type reactions and 1:1 coupling of six-membered halo(hetero)arenes and norbornene (NBE) derivatives, Pd-catalyzed 1:2 coupling of five-membered haloheteroarenes with NBEs was achieved to afford rigid nonplanar heterocycles. Pyra
Hetero-dicarbene complexes of palladium(II): Syntheses and catalytic activities
Yuan, Dan,Huynh, Han Vinh
, p. 6033 - 6043 (2014)
A series of Pd(II) dibromido complexes 2-6 bearing cis-chelating hetero-dicarbenes, which contain two different types of NHCs linked by a propylene chain, have been synthesized. In most cases, the N-methylbenzimidazolin-2-ylidene moiety was kept as one NHC donor, while the other one varies with different heterocyclic backbones. As an exception, the hetero-diNHC in complex 8 is derived by combining 1,2,4-triazole and indazole precursors instead. Analogous complexes 9-17, carrying more labile CF3CO2- or CH3CN ligands, were synthesized by reacting the aforementioned bromido complexes with AgO2CCF3 or AgOTf in CH3CN. A systematic catalytic comparison of 9-17 in the direct arylation of pentafluorobenzene with 4-chlorobromobenzene was carried out, and complexes that contain bulkier and less electron-donating ligands were found to be more active. Complex 12, carrying the mesitylimidazolin-2-ylidene unit, proved to be the most efficient, and its activity was also tested in the direct arylation of tetrafluorobenzenes.
Amine-functionalized indazolin-3-ylidene complexes of palladium(II) by postmodification of a single precursor
Bernhammer, Jan C.,Singh, Harvenjit,Huynh, Han Vinh
, p. 4295 - 4301 (2014)
A series of five trans-[PdBr2(amine)(indy)] complexes (amine = diethylamine, dipropylamine, dibutylamine, diisobutylamine, morpholine; indy = indazolin-3-ylidene) with pendant teriary amine functionalities in the side chain of the NHC ligand has been prepared by postcoordinative modification of a single bromoalkyl-functionalized precursor complex. This approach allows for a synthesis of functionalized N-heterocyclic carbene complexes more efficient than the metalation of prefunctionalized azolium salts. All complexes have been fully characterized, and the molecular structures of three complexes are reported. A correlation exists between the 13C NMR shift of C carbene and the pKb values of the coordinated amines. Furthermore, all complexes were found to be active catalysts for the direct arylation of 1-methylpyrrole with good to excellent yields.
Palladium-Catalyzed Oxidative Arylation of 1H-Indazoles with Arenes
Gambouz, Khadija,Abbouchi, Abdelmoula El,Nassiri, Sarah,Suzenet, Franck,Bousmina, Mostapha,Akssira, Mohamed,Guillaumet, Gérald,El Kazzouli, Sa?d
supporting information, p. 7435 - 7439 (2020/11/30)
A simple method for the direct Pd(OAc)2-catalyzed oxidative arylation of inactivated 1H-indazole derivatives with simple arenes is reported. This method exhibits good reaction efficiency and good functional-group tolerance. Using the developed method, 28 arylated products were prepared in yields up to 80 %.
Direct N-Alkylation and Kemp Elimination Reactions of 1-Sulfonyl-1H-Indazoles
Tang, Meng,Chu, Bingjie,Chang, Xiaowei
, p. 2109 - 2116 (2018/07/31)
The reactions of 1-sulfonyl-1H-indazoles under basic conditions are discussed, and the direct N-alkylation and Kemp elimination reactions of these compounds are reported. A series of 2-(p-tosylamino)benzonitriles and N-alkyl indazoles were prepared in good yields. Moreover, the 2-(p-tosylamino)benzonitriles could be transformed into a diverse range of important derivatives in a one-pot reaction. This method was successfully applied to the total syntheses of quindolinone and cryptolepinone; quindolinone was prepared in a one-pot reaction from 1-sulfonyl-1H-indazole.