Selective Synthesis of Various Photofunctional Multinuclear Complexes Using a Combination of the Mizoroki–Heck Reaction and the Homo-coupling Reaction
01 Jan 2022-pp 33-57
About: The article was published on 2022-01-01 and is currently open access. It has received None citations till now. The article focuses on the topics: Heck reaction & Coupling reaction.
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TL;DR: s, or keywords if they used Heck-type chemistry in their syntheses, because it became one of basic tools of organic preparations, a natural way to make organic preparations.
Abstract: s, or keywords if they used Heck-type chemistry in their syntheses, because it became one of basic tools of organic preparations, a natural way to
3,373 citations
1,832 citations
TL;DR: Activated and non-activated aryl bromides undergo smooth ligand-less Heck reactions, provided low amounts of palladium salts such as Pd(OAc)2 are used.
579 citations
TL;DR: Palladium(II) diacetate reacted with water (1 equiv/Pd) and (R)-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl ((R)-BINAP) (3 equiv./Pd), in benzene in the presence of Et3N to give the palladium(0) species Pd[(R)-bINAP]2, and the reduction of Pd(PPh3)4 and OPPh3.
Abstract: Palladium(II) diacetate reacted with water (1 equiv./Pd) and (R)-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl ((R)-BINAP) (3 equiv./Pd) in benzene in the presence of Et3N to give the palladium(0) species Pd[(R)-BINAP]2 (1 equiv./Pd), (R)-BINAP monoxide (1 equiv./Pd), and Et3N·HOAc (2 equiv./Pd). The progress of reaction strongly affected by the content of water in the reaction solution. The reduction of Pd(OAc)2 in the presence of PPh3 proceeded in a similar process to give Pd(PPh3)4 and OPPh3.
204 citations
TL;DR: This review is organized by the types of reactions in the following order: Sonogashira and Cadiot-Chodkiewicz, Suzuki and Negishi, Heck, Stille, and oxidative/reductive homocoupling reactions.
Abstract: More than a century after the founding of coordination chemistry by Alfred Werner, inorganic chemistry has branched into organometallics, bioinorganic, polymer, and solid state/materials chemistry. A common feature of the new frontiers of inorganic chemistry is the increasing degree of complexity of ligands and the rich functionalities of the resultant compounds. The desire to achieve complex inorganic species of either novel functionality or intricate topology provides stimulus for new synthetic strategies with improved efficiency and selectivity. One of the emerging strategies invokes the formation of C-C bond at the coordinated ligands distant from the metal center. This approach takes advantage of Pd-catalyzed cross-coupling reactions that have been explored extensively by organic chemists with well-defined catalysts and the scope of substrates. Successful peripheral modifications include the Sonogashira, Suzuki, Negishi, Heck, and Stille reactions. Alternatively, peripheral C-C bond formation can also be achieved through homocoupling reactions such as the Glaser reaction and the olefin metathesis reaction. The earliest example of peripheral modification appears to be the work of Schlögl and Steyrer, where the series of Fc-(C≡C)2m-Fc (m ) 1-4) type compounds was prepared from the oxidative coupling of Fc-(C≡C)mH with excess Cu(OAc)2 in pyridine/MeOH (Eglinton conditions). The other early example was based on the nickel complex of octaethylporphyrin (Ni(OEP)): the meso-bromovinyl compound was converted to the meso-acetylene derivative (1), which was converted to a butadiyne-bridged dimer (2) under the Eglinton conditions (Scheme 1). The pioneering exploration of peripheral cross-coupling is probably attributed to those of Smith and co-workers, where the -olefinated porphyrins (4) were prepared from the -mercurated porphyrins (3) under Heck coupling conditions (Scheme 1). While the reports on peripheral C-C bond formation were sparse early on, this area exploded in the 1990s with major efforts on metalloporphyrins and metal-bipy/terpy compounds. To date, the peripheral modification approach becomes omnipresent in all areas of inorganic chemistry, and notable applications range from the formation of robust molecular scaffolds to the syntheses of metal-bioconjugates under mild conditions. This review is organized by the types of reactions in the following order: Sonogashira and Cadiot-Chodkiewicz, Suzuki and Negishi, Heck, Stille, and oxidative/reductive homocoupling reactions. The peripheral olefin metathetic reactions were recently covered in the excellent review by Bauer and Gladysz and will not be included here. Finally, the subject of this review should not be confused with the activation of small molecules via metal coordinationsa topic key to homogeneous catalysis that has
114 citations