Nickel-phosphine complex catalyzed coupling reaction of grignard reagents with alkenyl or aryl sulfides

Okamura, Hisashi; Miura, Morikazu; Takei, Hisashi

doi:10.1016/s0040-4039(01)85876-7

Cited by 156 publications

(35 citation statements)

References 18 publications

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“…349 The use of 3 mol% Ni(PPh 3 ) 2 Cl 2 was found to be effective for the coupling of various organosulfides with Grignard reagents. Under these conditions, no reaction with alkyl sulfides as substrates was observed.…”

Section: Cross-couplings With Alkylmagnesium Reagentsmentioning

confidence: 99%

Advances in Transition Metal (Pd,Ni,Fe)-Catalyzed Cross-Coupling Reactions Using Alkyl-organometallics as Reaction Partners

2011

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Introduction 1418 1.1. List of Common Ligands 1419 2. Alkylzinc Reagents 1419 2.1. Synthesis of Alkylzinc Reagents 1419 2.2. Stability of Alkylzinc Reagents 1420 2.3. Cross-Coupling Reactions of Alkylzinc Reagents 1421 2.4. Palladium-Catalyzed Cross-Coupling Reactions of Alkylzinc Reagents 1423 2.4.1. Palladium-Catalyzed C(sp 2 )-C(sp 3 ) Negishi Coupling with Alkylzinc Reagents 1423 2.4.2. Palladium-Catalyzed C(sp 3 )-C(sp 3 ) Negishi Coupling with Alkylzinc Reagents 1427 2.4.3. Palladium-Catalyzed C(sp)-C(sp 3 ) Negishi Coupling with Alkylzinc Reagents 1428 2.4.4. Formation of Ketones via Palladium-Catalyzed Negishi Coupling with Alkylzinc Reagents 1429 2.5. Nickel-Catalyzed Cross-Coupling Reactions of Alkylzinc Reagents 1429 2.5.1. Nickel-Catalyzed C(sp 2 )-C(sp 3 ) Negishi Coupling with Alkylzinc Reagents 1429 2.5.2. Nickel-Catalyzed Carboxylations with Alkylzinc Reagents 1430 2.5.3. Nickel-Catalyzed C(sp 3 )--(sp 3 ) Negishi Coupling with Alkylzinc Reagents 1430 2.5.4. Mechanistic Insights in Nickel-Catalyzed Cross-Couplings 1433 3.

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Section: Cross-couplings With Alkylmagnesium Reagentsmentioning

confidence: 99%

Advances in Transition Metal (Pd,Ni,Fe)-Catalyzed Cross-Coupling Reactions Using Alkyl-organometallics as Reaction Partners

2011

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“…108-109°C); R f = 0.8 (hexanes). 1 General Procedure for Nickel-Catalysed Cross-Coupling Reaction with Methyl/Phenyl Grignard Reagents: A solution of bis(triphenylphosphanyl)nickel dichloride [29] (0.98 g, 15 mol %) in dry benzene (15 mL) was added dropwise under nitrogen to a suspension of methylmagnesium iodide/phenylmagnesium bromide [15 mmol, prepared from 0.36 g (0.015 g atom) of magnesium turnings and 15 mmol of methyl iodide/phenyl bromide] in dry ether (25 mL), and the reaction mixture was stirred at room temperature for 15 min. A solution of 4c or 20 (5 mmol) in dry benzene (25 mL) was added, and the reaction mixture was heated at reflux for 12 h. It was then cooled, poured into 100 mL of saturated NH 4 Cl solution, extracted with diethyl ether (2 × 100 mL), dried (Na 2 SO 4 ) and evaporated to give crude residues of 6 or 22, which were purified by column chromatography over silica gel with hexane/ethyl acetate (99:1) as eluent.…”

Section: Fluoranthene (5)mentioning

confidence: 99%

Efficient Routes to Acenaphthylene‐Fused Polycyclic Arenes/Heteroarenes and Heterocyclic Fluoranthene Analogues

et al. 2005

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The acenaphthenone-derived α-oxoketene dithioacetal 2 has been subjected to various [3 + 3] aromatic and heteroaromatic annulation and other heterocyclization reactions previously developed in our laboratory, providing short and efficient routes to a diverse range of known and unknown acenaphtho-annulated linear and angular PAHs, heteroaromatics and five-membered heterocycles in good yields. Thus, benzo-and naphthoannulation of 2 with various allyl and benzyl Grignard reagents afforded substituted fluoranthenes 4a-c and benzo[k]fluoranthene 8, respectively, in good yields. Similarly, the parent benzo[j]fluoranthene 15a and its substituted derivative 16b have been synthesized by baseinduced conjugate 1,4-addition of arylacetonitriles to 2, followed by acid-induced cyclization of the conjugate adducts 12a-b to give 13a-b and subsequent further transformations. The adducts obtained by 1,4-addition of anions derived from acetophenone and acenaphthenone were subjected to heterocyclization in the presence of ammonium acetate to

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“…29 We have also shown that aliphatic sulfonyl chlorides are also excellent electrophiles. 31 Among the earliest, most economical and useful nucleophilic partners are the Grignard reagents, which can be coupled with all kinds of electrophilic partners such as sulfides, [32][33][34][35][36][37][38][39] sulfoxides 32,40 sulfoximines, [41][42][43][44][45] sulfones, 46-52 sulfonic esters, [53][54][55] and sulfonamides 56 in the presence of nickel catalysts.…”

Section: Introductionmentioning

confidence: 99%

Palladium-catalyzed desulfinylative C–C allylation of Grignard reagents and enolates using allylsulfonyl chlorides and esters

Volla¹,

Dubbaka²,

Vogel³

2009

Tetrahedron

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a b s t r a c t 2-Methylprop-2-ene-, prop-2-ene-, 1-methylprop-2-ene-, and (E)-but-2-enesulfonyl chlorides have been used as electrophilic partners in desulfinylative palladium-catalyzed C-C coupling with Grignard reagents and sodium salts of dimethyl malonate and methyl acetoacetate. Neopentyl alk-2-ene sulfonates can also be used as electrophilic partners in desulfinylative allylic arylations and allylic alkylations. The regioselectivity of the allylic arylation and alkylation depends on the nature of the catalyst. With PdCl 2 (PhCN) 2 , (E)-crotyl derivatives are formed in high regioselectivity using either 1-methylprop-2-eneor (E)-but-2-enesulfonyl chloride.

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Nickel-phosphine complex catalyzed coupling reaction of grignard reagents with alkenyl or aryl sulfides

Cited by 156 publications

References 18 publications

Advances in Transition Metal (Pd,Ni,Fe)-Catalyzed Cross-Coupling Reactions Using Alkyl-organometallics as Reaction Partners

Advances in Transition Metal (Pd,Ni,Fe)-Catalyzed Cross-Coupling Reactions Using Alkyl-organometallics as Reaction Partners

Efficient Routes to Acenaphthylene‐Fused Polycyclic Arenes/Heteroarenes and Heterocyclic Fluoranthene Analogues

Palladium-catalyzed desulfinylative C–C allylation of Grignard reagents and enolates using allylsulfonyl chlorides and esters

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