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Application of N-halo reagents in ..

Since Brown’s discovery of the hydroboration reaction, ­organoboron compounds have found wide application in organic synthesis. [] The synthesis of functional organoboranes has mostly relied on either the hydroboration of unsaturated hydrocarbons or the transmetallation between an organometallic precursor and an appropriate boron compound.

Synthesis of new halo-containing acetylenes and their application to ..

[225] Organosilicon Reagents: Synthesis and Application to Palladium-Catalyzed Cross-Coupling Reactions (with M. H. Ober) Aldrichimica Acta 2003, 36, 75-85. []

the application of N-halo compounds in organic ..

Stereospecific synthesis of allylic amines by aminomethylation of organocopper reagents” 1980, , 3763-3766.

Platinum-catalyzed 1,4-diboration of 1,3-diene 2 with 1 produces (Z)-1,2,3,4-tetraboryl-2-butene in quantitative yield as a single stereoisomer (Scheme ). The resulting tetraboryl-2-butene undergoes triple aldehyde addition in a one-pot manner to give 2,3-bis(alkylidene)-1,5-anti-diols as a single stereoisomer.) The cascade reaction involves sequential conversion of four C–B bonds into two C–C bonds and one C=C bond with perfect stereocontrol. One-pot preparation–triple carbonyl addition starting with 2 is also possible. These features clearly demonstrate the versatility of polymetalated compounds as reagents for organic synthesis with high efficiency.

Synthesis of Acyl Alkenylindium Reagents and Their Application in the Synthesis of (Z)-α,β-Unsaturated Ketones via Palladium-Catalyzed Cross-Coupling Reaction, 2015,

Synthesis of nitro compounds - Organic chemistry

Application of cyclic phosphonamide reagents in the total synthesis of natural products and biologically active molecules

Based on the novel concept, the authors designed gem-dimetalation of lithium carbenoids with such metal–metal compounds as B–B and B–Si (Scheme ). Thus, they envisioned that gem-diboryl and gem-silylboryl products should result via a sequence of reactions of (1) borate formation and (2) 1,2-migration of a boron or silicon atom from the negatively charged borate centers to the carbenoid carbons in a 1,2-fashion with elimination of a halogen atom.) Actually the designed sequence did work well.) Consequently, repertoire of gem-silylboryl and gem-diboryl compounds are largely expanded, and organic synthesis utilizing those bifunctional reagents has dramatically advanced. This review focuses on not only gem-diboryl but also vic-diboryl compounds illustrated in Figure and summarizes the preparations and selective transformations for organic synthesis.)

In sharp contrast, gem-dimetalation using such metal–metal compounds has remained unexplored.) In 1976, Kitatani, Hiyama, and Nozaki reported stereoselective one-pot dialkylation of gem-dihalocyclopropanes with diorganocuprate and alkyl halide. The reaction is considered to proceed through generation of an ate-type carbenoid by bromine-copper exchange at the less hindered site, consecutive alkyl 1,2-migration from the negatively charged copper to the carbenoid carbon with inversion of configuration, and the second alkylation of the resulting copper reagent with methyl iodide (Scheme ).) This type of transformation is disclosed now to be applicable to not only cyclopropylidene- but also alkylidene-type carbenoid reagents with a variety of metals.) Worthy to note is that an SN2 type substitution reaction with inversion of configuration at the carbogenic center, which is otherwise inert to conventional nucleophilic substitution reaction.

02/06/2007 · J. Iran. Chem. Soc., Vol. 4, No. 2, June 2007, pp. 126-174. JOURNAL OF THE Iranian Chemical Society Application of N-Halo Reagents in Organic Synthesis …
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Piperidine synthesis - Organic chemistry

Tamejiro Hiyama was born in Osaka, 1946. He started his academic career in 1972 as Research Associate at Kyoto University, received the Doctor of Engineering degree in 1975 (Kyoto University, Mentor Hitosi Nozaki), and spent a postdoctoral year (Harvard University, Yoshito Kishi). In 1981, he joined Sagami Chemical Research Center as Research Fellow to start his own research team. There he was promoted to Senior Research Fellow and then to Executive Research Fellow before he moved in 1992 to Research Laboratory of Resources Utilization, Tokyo Institute of Technology, as Professor of Division of Newer Metal Resources. Since 1997, he is Professor of Organic Materials at Kyoto University. He studied and invented many new reactions including, the highly selective carbon-carbon bond formation with Cr reagents (Nozaki-Hiyama-Kishi reaction), the reaction of nitriles with magnesium ester enolates (Hiyama reaction), the cross-coupling reaction with organosilicon reagents (Hiyama coupling), the oxidative desulfurization-fluorination for synthesis of organofluorine compounds, the carbostannylation and carbocyanation of alkynes, novel polysilacage compounds for electronic materials, novel liquid crystalline compounds for display in addition to carbenoid reagens for organic synthesis. He received Young Chemist Award of the Chemical Society of Japan in 1980, Japan Liquid Crystal Society Award in 2004, Synthetic Organic Chemistry Award in 2007, and is going to receive the CSJ Award, 2008. His current research interest extends to new organometallic reagents for selective organic synthesis, organofluorine and organosilicon chemistry, synthesis of biologically active substances, design and synthesis of novel functionality molecules and materials.

1,2-Amino Alcohols and Their Heterocyclic Derivatives …

Dimetalated organic compounds have recently emerged as versatile reagents for organic synthesis because such bifunctional compounds allow us to synthesize target organic frameworks very efficiently through multiple bond formations in a single operation or stepwise transformations in one-pot.) Furthermore, organodimetallic compounds can serve as valuable precursors of polyfunctional organometallic reagents.) Therefore, it is of great importance to develop efficient preparations as well as chemo-, regio-, stereo-, and enantioselective reactions of dimetalated compounds. Simultaneous incorporation of two metals into organic substrates with reagents having metal–metal linkage is a highly attractive approach as the preparative method in view of atom economy and straightforward strategy (Scheme ). Indeed, transition-metal catalyzed cleavage of the metal–metal linkage such as B–B, B–Si, B–Sn, Mg–Si, Mg–Zn, Mg–Sn, Al–Si, Al–Sn, Si–Si, Si–Sn, Si–Zn, Sn–Sn, and Sn–Zn, followed by addition to carbon–carbon unsaturated bonds have been well-described as efficient synthesis of vic-dimetalated compounds.)

Tetrahydrofuran, anhydrous, ≥99.9%, inhibitor-free | …

Vanadium(II) chloride has found application in modern organic synthesis in part because its redox potential (+0.255 V) is greater than the SnII-SnIII couple (-0.15 V) although lower than CrII-CrIII (+0.41 V) or TiII-TiIII (+0.37 V). A variety of synthetic transformations have been documented.

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