154237-62-4Relevant academic research and scientific papers
Heterocyclic Allylsulfones as Latent Heteroaryl Nucleophiles in Palladium-Catalyzed Cross-Coupling Reactions
Markovic, Tim,Murray, Philip R.D.,Rocke, Benjamin N.,Shavnya, Andre,Blakemore, David C.,Willis, Michael C.
, p. 15916 - 15923 (2018/11/23)
Heterocyclic sulfinates are effective reagents in palladium-catalyzed coupling reactions with aryl and heteroaryl halides, often providing high yields of the targeted biaryl. However, the preparation and purification of complex heterocylic sulfinates can be problematic. In addition, sulfinate functionality is not tolerant of the majority of synthetic transformations, making these reagents unsuitable for multistep elaboration. Herein, we show that heterocyclic allylsulfones can function as latent sulfinate reagents and, when treated with a Pd(0) catalyst and an aryl halide, undergo deallylation, followed by efficient desulfinylative cross-coupling. A broad range of allyl heteroarylsulfones are conveniently prepared, using several complementary routes, and are shown to be effective coupling partners with a variety of aryl and heteroaryl halides. We demonstrate that the allylsulfone functional group can tolerate a range of standard synthetic transformations, including orthogonal C- and N-coupling reactions, allowing multistep elaboration. The allylsulfones are successfully coupled with a variety of medicinally relevant substrates, demonstrating their applicability in demanding cross-coupling transformations. In addition, pharmaceutical agents crizotinib and etoricoxib were prepared using allyl heteroaryl sulfone coupling partners, further demonstrating the utility of these new reagents.
Arylation, Vinylation, and Alkynylation of Electron-Deficient (Hetero)arenes Using Iodonium Salts
Liu, Chuan,Wang, Qiu
supporting information, p. 5118 - 5121 (2016/10/14)
Arylation, vinylation, and alkynylation of electron-deficient arenes and heteroarenes have been achieved by chemoselective C-H zincation followed by copper-catalyzed coupling reactions using iodonium salts. This approach offers a direct and general access to a wide scope of (hetero)biaryls as well as alkenylated and alkynylated heteroarenes under mild conditions. It is particularly useful and valuable for the rapid and modular synthesis of diverse (hetero)aryl compounds, as demonstrated in the synthesis of transient receptor potential vanilloid 1 (TRPV1) antagonists and angiotensin II receptor type 1 (AT1 receptor) antagonists.
P,N,N-Pincer nickel-catalyzed cross-coupling of aryl fluorides and chlorides
Wu, Dan,Wang, Zhong-Xia
, p. 6414 - 6424 (2014/08/18)
P,N,N-Pincer nickel complexes [Ni(Cl){N(2-R2PC6H 4)(2′-Me2NC6H4)}] (R = Ph, 3a; R = Pri, 3b; R = Cy, 3c) were synthesized and their catalysis toward the Kumada or Negishi cross-coupling reaction of aryl fluorides and chlorides was evaluated. Complex 3a effectively catalyzes the cross-coupling of (hetero)aryl fluorides with aryl Grignard reagents at room temperature. Complex 3a also catalyzes the cross-coupling of (hetero)aryl chlorides and arylzinc reagents at 80 °C with low catalyst loadings and good functional group compatibility. the Partner Organisations 2014.
Design, Synthesis, Structural Studies, Biological Evaluation, and Computational Simulations of Novel Potent AT1 Angiotensin II Receptor Antagonists Based on the 4-Phenylquinoline Structure
Cappelli, Andrea,Mohr, Gal La Pericot,Gallelli, Andrea,Rizzo, Milena,Anzini, Maurizio,Vomero, Salvatore,Mennuni, Laura,Ferrari, Flora,Makovec, Francesco,Menziani, M. Cristina,De Benedetti, Pier G.,Giorgi, Gianluca
, p. 2574 - 2586 (2007/10/03)
Novel AT1 receptor antagonists bearing substituted 4-phenylquinoline moieties instead of the classical biphenyl fragment were designed and synthesized as the first step of an investigation devoted to the development of new antihypertensive agen
Synthesis of functionally substituted unsymmetrical biaryls via a novel double metal catalyzed coupling reaction
Miller, Joseph A.,Farrell, Robert P.
, p. 7275 - 7278 (2007/10/03)
Unsymmetrical biaryls containing 'reactive' functional groups (e.g., nitrile or ester groups) can be synthesized in an efficient manner by the direct Ni- or Pd-catalyzed coupling of aryl halides (X = Cl, Br, I) with aryl Grignard (or -lithium) reagents, provided that a catalytic amount of a Zn or Cd salt is also present.
