Novel Stereoselective Cyclization via .pi.-Allylnickel Complex Generated from 1,3-Diene and Hydride Nickel Complex

Sato, Yoshihiro; Takimoto, Masanori; Hayashi, Kôji; Katsuhara, Takao; Takagi, Koji; Mori, Miwako

doi:10.1021/ja00100a061

Cited by 148 publications

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“…Recently, we succeeded in developing a nickel-promoted cyclization of v-formyl-1,3-dienes [4]. The reaction of v-formyl-1,3-diene 1 using a stoichiometric amount of a low-valent nickel complex 2, generated by reduction of Ni(acac) 2 with DIBAL Á/H in the presence of PPh 3 , afforded the cyclized products 3-I and 3-T in a stereoselective manner with respect to the substituents on the cycloalkane ring (Eq.…”

Section: Introductionmentioning

confidence: 99%

Further studies on Ni(0)-catalyzed cyclization of a branched 1,3-diene and tethered aldehyde via oxa-nickelacycle intermediate

Sato

Takanashi

Hoshiba

et al. 2003

Journal of Organometallic Chemistry

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Section: Introductionmentioning

confidence: 99%

Further studies on Ni(0)-catalyzed cyclization of a branched 1,3-diene and tethered aldehyde via oxa-nickelacycle intermediate

Sato

Takanashi

Hoshiba

et al. 2003

Journal of Organometallic Chemistry

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“…The electron-withdrawing silyl ligand may increase the Lewis acidity of platinum(II), thus allowing coordination and the next insertion of the carbonyl group. The proposed mechanism, involving a nucleophilic π-allyl transition metal species, is also reported in the nickel-catalyzed hydrosilylation of a diene having a carbonyl group [140].…”

Section: Addition To 12-dienes (Allenes) and 13-dienesmentioning

confidence: 77%

Hydroboration, Diboration, Silylboration, and Stannylboration

Miyaura

2001

Catalytic Heterofunctionalization

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“…Indeed, Mori et al realized this idea in the cyclization reaction of o-dienyl aldehyde 5.11 (Eq. (5.5)) [26]. That is, when a toluene solution of 5.11, Ni(cod) 2 (100 mol%), PPh 3 (200 mol%), and Et 3 SiH (150 mol%) was stirred at 0 C, an intramolecular allylation of aldehyde and trapping of the aldehyde oxygen with silicon took place to give 5.12-i with excellent stereoselectivity.…”

Section: ð5:4þmentioning

confidence: 99%

Reaction of Dienes and Allenes

Kimura

Tamaru

2005

Modern Organonickel Chemistry

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1,3-Butadiene and isoprene (2-methyl-1,3-butadiene) are among the most important building blocks both in the laboratory and in the chemical industry. 1,3-Butadiene (DH f ¼ þ26:1) and 1,2-butadiene (methylallene DH f ¼ þ38:8) are highly unsaturated and labile even toward relatively unreactive reagents, such as O 2 in air, and undergo polymerization during storage.Although the [4þ2]cycloaddition -the so-called Diels-Alder reaction -of butadiene to afford 4-vinylcyclohexene is a thermally permitted process, it only proceeds under harsh conditions (e.g., at 250 C under high pressure). In contrast, nickel complexes promote the [4þ2]cycloaddition under milder conditions (e.g., at 0 C under ambient pressure) [1]. Furthermore, the complexes even promote thermally forbidden [4þ4]cycloaddition and other reactions. Many other 1,3-dienes and allenes are also subject to dimerization, oligomerization, and polymerization under nickel catalysis, and hence serve as useful C4 and C3 carbon resources for a variety of organic syntheses.This chapter deals with recent developments in the nickel-catalyzed functionalizations of conjugated dienes and allenes, and incorporates the following topics: 1) dimerization and polymerization; 2) allylic and homoallylic alkylation of carbonyl compounds (dienes and allenes as nucleophiles); and 3) 1,2-and 1,4-addition reactions of reagents X-Y toward dienes and allenes. 5.1Dimerization and Polymerization of 1,3-Dienes Nickel complexes are extremely effective catalysts for the dimerization and polymerization of dienes. The catalytic reactions are described in Chapter 6, Section 6.4. The major subject of this section relates to the structures and reactivities of Ni(II)Á(butadiene) 2 complexes (the stoichiometric reactions) and recent developments in the field of polymerization.Modern Organonickel Chemistry. Edited by Y. Tamaru

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Novel Stereoselective Cyclization via .pi.-Allylnickel Complex Generated from 1,3-Diene and Hydride Nickel Complex

Cited by 148 publications

References 0 publications

Further studies on Ni(0)-catalyzed cyclization of a branched 1,3-diene and tethered aldehyde via oxa-nickelacycle intermediate

Further studies on Ni(0)-catalyzed cyclization of a branched 1,3-diene and tethered aldehyde via oxa-nickelacycle intermediate

Hydroboration, Diboration, Silylboration, and Stannylboration

Reaction of Dienes and Allenes

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