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An efficient method for carbon–carbon bond formation is described. The process employs the palladium-catalyzed and copper-mediated cross-coupling of quinoline-2-(1 H)-thiones with arylboronic acids or alkynes through C–S bond cleavage without an inert atmosphere. The method provides rapid and general access to a diverse range of 2-substituted quinolines in a single step from a wide range of quinoline-2-(1 H)-thiones and arylboronic acids or alkynes. [ABSTRACT FROM AUTHOR]

Abstract: Organic phosphonates and their derivatives are an important class of compounds in a variety of fields, especially medicinal chemistry, materials chemistry, agrochemistry and catalysis. For example, phosphonate esters and carbamoylphosphonates are matrix metalloproteinase (MMP) inhibitors, antimetastatic agents and antitumor agents. Phosphonate esters are usually prepared via a multistep transformation from a phenol and an organohalide and require toxic phosphorus halides and aryl/alkyl halides. , Palladium‐catalyzed couplings of an aryl halide (ArX) with a P−H compound, which were developed by Hirao and co‐workers, are now typically used as efficient and substrate‐tolerant methods for preparing phosphonates (Scheme 1). , Recently, great advances were made in the synthesis of phosphonate esters via metal‐catalyzed C−P bonds couplings of H‐phosphonates with C−X compounds (X=B, N, O, S and Si). Despite these clear advances, metal‐catalyzed coupling reactions of P−H with C−X(H) are still limited by the need for costly noble metal catalysts. [ABSTRACT FROM AUTHOR]

The Pd‐catalyzed cross‐coupling reaction of 1, 2‐di(pyrimidin‐2‐yl) disulfides with heterocyclic amines including 2‐amino pyrimidines and 1,3,4‐thiadiazol‐2‐amines to deliver symmetrical C‐N coupling products in moderate to good yields is reported. This method provides an opportunity for synthesis of bioactive molecules and pharmaceutically interesting compounds containing heterocycle motifs. The reported protocol shows good functional group compatibility, and provides a new strategy for preparation of C2‐amination pyrimidine derivatives from heterocyclic disulfides. [ABSTRACT FROM AUTHOR]

The straightforward visible-light-induced synthesis of stilbene compounds via the cross-coupling of nitroalkenes and diazonium tetrafluoroborates under transition-metal-free conditions is described. The protocol uses green LEDs as light sources and eosin Y as an organophotoredox catalyst. Broad substrate scope and exclusive selectivity for the (E)-configuration of stilbenes are observed. This protocol proceeds via a radical pathway, with nitroalkenes serving as the radical acceptor, and the nitro group is cleaved during the process. [ABSTRACT FROM AUTHOR]

A simple and practical denitrated coupling reaction of nitroalkenes with various alkenes using a nickel catalyst and triethoxysilane [(EtO)3SiH] as reducing agent was achieved. Under mild reaction conditions, both aliphatic and aromatic alkenes could react with nitroalkenes to obtain a series of olefins with different functional groups in satisfactory yields under an air atmosphere, which were previously difficult or impossible to access. [ABSTRACT FROM AUTHOR]

Iron-catalyzed Kumada cross-coupling reactions of pyrimidin-2-yl phosphates and Grignard reagents are described. The reaction proceeds at room temperature with a short reaction time of 15 minutes, and the corresponding products are obtained with moderate to high yields. A wide array of C2-functionalized pyrimidines has been prepared in moderate to good yields and many functional groups are well tolerated. [ABSTRACT FROM AUTHOR]

Pyrimidin-2-yl sulfonates, as a reaction partner, can be easily prepared from inexpensive commercial materials and are efficiently cross-coupled with arylboronic acids and terminal alkynes by using Pd(OAc)2-catalyzed Suzuki and Sonogashira reactions. A wide array of C2-functionalized pyrimidines have been prepared in good to excellent yields. 2-Arylpyridines and 2-(oct-1-ynyl)pyridine were also synthesized. [ABSTRACT FROM AUTHOR]

Ni-catalyzed Suzuki–Miyaura cross-coupling reactions of pyrimidin-2-yl phosphates, tosylates and pivalates with arylboronic acids were described. A wide array of functionalized pyrimidines have been prepared in impressive yields and show good tolerance towards wide substrate scope. [ABSTRACT FROM AUTHOR]

CuSO 4 ·5H 2 O and NaAsc catalyzed hydroxylation and C–O/C–S cross-coupling reactions of aryl halides with phenols or 4-methylbenzenethiol were described. A wide range of substrates and test cases highlight the synthetic utility of the approach. A series of phenols, diaryl ethers, alkylaryl ethers, and diaryl thioethers were synthesized in high yield. [ABSTRACT FROM AUTHOR]

An Fe(III)-catalyzed cross-coupling of N-heteroaromatic tosylates with aryl and alkyl Grignard reagents is presented. [ABSTRACT FROM AUTHOR]

Abstract: A domino S–N and C–N coupling/oxidative aromatization process to synthesize 2-aminothio-phenylpyrimidines and 2-amino-phenylpyrimidines by S–N and C–N cross-coupling reactions is described. This methodology couples 3,4-dihydropyrimidine-2-thiones and secondary amines catalyzed by molecular iodine. Remarkably the C–N coupled product was obtained via a desulfitative coupling-aromatization reaction in one-pot reaction. [Copyright &y& Elsevier]

The article presents the cross coupling reaction of N-heterocyclic compounds with 1,2-Di(pyrimidin-2-yl) disulfides using copper.

Furthermore, similar reaction conditions also allow the C-S coupling of aryl halides with 4-methylbenzenethiol. [ABSTRACT FROM AUTHOR]

Pyrimidine- and pyridine phosphates react with alkyl and aryl Grignard reagents in the presence of Fe(acac)3 under mild conditions to give the title compounds at room temperature within 15 minutes. [ABSTRACT FROM AUTHOR]

The title reactions between substituted pyrimidin-2-yl sulfonates [e.g. (I)] and arylboronic acids, terminal alkynes, or anilines give the cross-coupling products in good yields with wide substrate scope. [ABSTRACT FROM AUTHOR]

Arylboronic acids with strong electron-withdrawing groups (e.g., 4-CHO, 4-Ac or 4-COOH) do not react with compound (I) and also diallyl and di-tert-butyl disulfides fail in the reaction with (IIa). [ABSTRACT FROM AUTHOR]

The protocol for the chemoselective coupling reaction affords either a C-S bond in presence of ferrocene catalyst or the formation of a C-C bond in presence of palladium acetate catalyst. [ABSTRACT FROM AUTHOR]

The article presents chemical equations for article "Palladium(II) Catalyzed Suzuki/Sonogashira Cross-Coupling Reactions of Sulfonates: An Efficient Approach to C2-Functionalized Pyrimidines and Pyridines" by Z-J Quan and others, published in periodical "European Journal of Organic Chemistry in 2013.