24601-00-1Relevant academic research and scientific papers
Additive-Free Palladium-Catalyzed Decarboxylative Cross-Coupling of Aryl Chlorides
Daley, Ryan A.,Liu, En-Chih,Topczewski, Joseph J.
supporting information, p. 4734 - 4738 (2019/06/27)
The cross-coupling of sodium (hetero)aryl carboxylates with (hetero)aryl chlorides proceeds with 1 mol % palladium catalyst and does not require inorganic base, silver salts, or copper salts. This coupling uses two low energy partners, and the only stoichiometric byproducts are carbon dioxide and sodium chloride. The substrate scope includes less activated aryl chlorides and carboxylates (>25 examples). The palladium loading could be reduced to 0.1 mol %, and Buchwald-style precatalysts could be used.
One-pot preparation of pyrrole derivatives via the copper-catalyzed [4+1] annulation of propargylic amines with ethyl glyoxylate and phenylglyoxal in the presence of piperidine
Sakai, Norio,Suzuki, Hiroki,Hori, Hiroaki,Ogiwara, Yohei
, p. 63 - 66 (2016/12/23)
We describe how copper(II) chloride efficiently catalyzes the [4+1] annulation of propargylamines with either ethyl glyoxylate or phenylglyoxal functioning as a C1 unit, in the presence of piperidine, which leads to a straightforward and one-pot preparati
Copper(II)-Catalyzed [4+1] annulation of propargylamines with N,O-acetals: Entry to the synthesis of polysubstituted pyrrole derivatives
Sakai, Norio,Hori, Hiroaki,Ogiwara, Yohei
supporting information, p. 1905 - 1909 (2015/03/18)
Described herein is the CuCl2-catalyzed [4+1] annulation of a variety of propargylamines with N,O-acetals that function as a C1 unit, leading to the production of polysubstituted pyrrole derivatives. Three important features of the N,O-acetal during the [4+1] annulation series via 5-endo-dig cyclization are described: an enolizable substituent adjacent to the central sp3-carbon is required, the central sp3-carbon displays the functions of both an electrophile and a nucleophile, and liberation of the secondary amine smoothly leads to the aromatization. A CuCl2-catalyzed [4+1] annulation of propargylamines with N,O-acetals having an ester, a ketone, and an amide moiety, leading to the facile preparation of polysubstituted pyrrole derivatives is presented. This annulation series was achieved through 5-endo-dig cyclization and subsequent aromatization in one pot.
Total syntheses of (-)-hanishin, (-)-longmide B, and (-)-longmide B methyl ester via a novel preparation of N-substituted pyrrole-2-carboxylates
Cheng, Guolin,Wang, Xinyan,Bao, Hailin,Cheng, Chuanjie,Liu, Nan,Hu, Yuefei
, p. 1062 - 1065 (2012/04/23)
A novel preparation of N-substituted pyrrole-2-carboxylates has been developed based upon 1,3-dipolar cycloaddition and a conventional hydrogenolysis. By using this method as the key step, total syntheses of natural alkaloids (-)-hanishin, (-)-longmide B,
