Nickel-Catalyzed Suzuki-Miyaura Cross-Coupling Reaction of Naphthyl and Quinolyl Alcohols with Boronic Acids
A nickel-catalyzed C(sp3)-C(sp2) Suzuki cross-coupling of arylboronic acids and (hetero)naphthyl alcohols has been developed. A Ni(dppp)Cl2 complex showed the highest efficiency and broadest substrate scope. High functiona
Akkarasamiyo, Sunisa,Margalef, Jèssica,Samec, Joseph S. M.
Reactions of Quinolinecarbaldehydes with Arenes under Superelectrophilic Activation. NMR and DFT Studies of Dicationic Electrophilic Species
[Figure not available: see fulltext.] N,O-Diprotonated forms (dications) of various quinolinecarbaldehydes were theoretically studied by DFT calculations. It was found that the most reactive electrophilic dications are expected to be generated from 2- and
Borisova, Marina А.,Ryabukhin, Dmitry S.,Ivanov, Alexander Yu.,Boyarskaya, Irina A.,Spiridonova, Dar’ya V.,Kompanets, Mikhail O.,Vasilyev, Aleksander V.
p. 1007 - 1016
(2021/11/03)
Nickel-Catalyzed Electrochemical C(sp3)?C(sp2) Cross-Coupling Reactions of Benzyl Trifluoroborate and Organic Halides**
Reported here is the redox neutral electrochemical C(sp2)?C(sp3) cross-coupling reaction of bench-stable aryl halides or β-bromostyrene (electrophiles) and benzylic trifluoroborates (nucleophiles) using nonprecious, bench-stable NiCl2?glyme/polypyridine catalysts in an undivided cell configuration under ambient conditions. The broad reaction scope and good yields of the Ni-catalyzed electrochemical coupling reactions were confirmed by 50 examples of aryl/β-styrenyl chloride/bromide and benzylic trifluoroborates. Potential applications were demonstrated by electrosynthesis and late-stage functionalization of pharmaceuticals and natural amino acid modification, and three reactions were run on gram-scale in a flow-cell electrolyzer. The electrochemical C?C cross-coupling reactions proceed through an unconventional radical transmetalation mechanism. This method is highly productive and expected to find wide-spread applications in organic synthesis.
Luo, Jian,Hu, Bo,Wu, Wenda,Hu, Maowei,Liu, T. Leo
p. 6107 - 6116
(2021/02/01)
Pd-Catalyzed Alkylation of (Iso)quinolines and Arenes: 2-Acylpyridine Compounds as Alkylation Reagents
The first Pd-catalyzed alkylation of (iso)quinolines and arenes is reported. The readily available and bench-stable 2-acylpyridine compounds were used as an alkylation reagent to form the structurally versatile alkylated (iso)quinolines and arenes. The method affords a convenient pathway for the introduction of alkyl groups into organic molecules.
Feedstocks to Pharmacophores: Cu-Catalyzed Oxidative Arylation of Inexpensive Alkylarenes Enabling Direct Access to Diarylalkanes
A Cu-catalyzed method has been identified for selective oxidative arylation of benzylic C-H bonds with arylboronic esters. The resulting 1,1-diarylalkanes are accessed directly from inexpensive alkylarenes containing primary and secondary benzylic C-H bonds, such as toluene or ethylbenzene. All catalyst components are commercially available at low cost, and the arylboronic esters are either commercially available or easily accessible from the commercially available boronic acids. The potential utility of these methods in medicinal chemistry applications is highlighted.
Vasilopoulos, Aristidis,Zultanski, Susan L.,Stahl, Shannon S.
p. 7705 - 7708
(2017/06/20)
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