Tetracarbonyl nickel induced reaction of gem-dibromocyclopropanes with alcohols or amines.

Hirao, Toshikazu; Harano, Yoshiyuki; Yamana, Yoshihiro; Ohshiro, Yoshiki; Agawa, Toshio

doi:10.1016/s0040-4039(00)81628-7

Cited by 23 publications

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“…Synthetic methods using transition-metal enolates are required to be developed more because a variety of chemical protocols might be possible based on the reactivities of transition-metal enolates. 2 One of the striking protocols is dehydrosilylation of silyl enolates 2. Actually, the dehydrosilylation reaction through palladium enolates has been achieved by treatment of silyl enolates with palladium(II) acetate, as shown in Scheme 2, 3 which is considered to provide an important method in organic synthesis to introduce stereoselective ,-carbon-carbon double bonds to carbonyl compounds 1 regioselectively under milder reaction con-When I was a PhD course student, I made a number of serendipitous discoveries of dehydrosilylative oxidation; the results became a part of my doctoral thesis.…”

Section: Scheme 1 Transition-metal-induced Reaction Paths Of Main-gro...mentioning

confidence: 99%

Transformations of Main-Group Organometallics Induced by Transition Metals

Hirao¹,

Amaya²

2022

Synlett

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The oxidative dehydrometallation of silyl or boron enolates is induced by palladium(II) catalyst to result in the versatile introduction of α,β-unsaturated carbon–carbon double bonds via palladium enolates. Selective oxidative cross- and homo-coupling reactions of silyl or boron enolates induced by vanadium(V) oxidant provide a selective synthetic method for accessing 1,4-dicarbonyl compounds in a nucleophile-nucleophile coupling mode. The ligand coupling reaction of main-group organometallic compounds induced by vanadium(V) oxidant provides a unique method for intramolecular carbon–carbon bond formation of nucleophiles. The last two reactions are a complementary strategy for the nucleophile-electrophile coupling reaction. The dehydrometallation and coupling reactions probably proceed through two- and one-electron oxidation processes, respectively.1 Introduction2 Palladium-Catalyzed Dehydrometallation3 Homo- and Cross-Coupling of Main-Group Organometallic Compounds4 Oxidative Ligand Coupling of Main-Group Organometallic Compounds5 Conclusion

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Section: Scheme 1 Transition-metal-induced Reaction Paths Of Main-gro...mentioning

confidence: 99%