Nickel-induced conversion of carbon-oxygen into carbon-carbon bonds. One-step transformations of enol ethers into olefins and aryl ethers into biaryls

Wenkert, Ernest; Michelotti, Enrique L.; Swindell, Charles S.

doi:10.1021/ja00502a074

Cited by 372 publications

(163 citation statements)

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“…Since the discovery of the metal-catalysed reaction by Kumada and Corriu in the early 1970s [45,46], many ligands have been reported, especially (chelating) diphosphines [47][48][49][50][51][52][53][54][55][56][57], but very few examples of metal-imidazolium salt systems have been reported. Moreover, catalytic systems involving the reaction of unactivated aryl chlorides with aryl Grignard reagents have been described only recently [58,59].…”

Section: Catalytic Studiesmentioning

confidence: 99%

Nickel(II) complexes with bifunctional phosphine–imidazolium ligands and their catalytic activity in the Kumada–Corriu coupling reaction

Wolf¹,

Labande²,

Daran³

et al. 2006

Journal of Organometallic Chemistry

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Zwitterionic Ni(II) complexes of type NiX 3 (NCN + ), (NCN + = 1-(2-diphenylphosphinoethyl)-3-(2,4,6-trimethylphenyl)imidazolium and X = Cl, 6; Br, 7), have been prepared by addition of NCN + bromide (1a) or tetrafluoroborate (1b) to NiX 2 L, and characterised by X-ray crystallography. They have been used as catalytic precursors in the Kumada-Corriu coupling reaction between phenylmagnesium chloride and 4-chloroanisole, yielding high catalytic activities. Stoechiometric deprotonation investigations did not provide clear evidence for the formation of coordinated carbene species.

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Section: Catalytic Studiesmentioning

confidence: 99%

Nickel(II) complexes with bifunctional phosphine–imidazolium ligands and their catalytic activity in the Kumada–Corriu coupling reaction

Wolf¹,

Labande²,

Daran³

et al. 2006

Journal of Organometallic Chemistry

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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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“…As early as in 1979, Wenkert et al 9,10) reported the first Ni-catalyzed Kumada-Tamao type (Mg) [9][10][11][12][13][14][15][16][17][18][19][20][21][22][23] reaction, in which aryl methyl ether (ArOMe) acted as the electrophilic partner, and this is now recognized as the first example of Ni-catalyzed activation of an inert C-O bond. However, this breakthrough was overlooked for decades, until quite recently.…”

mentioning

confidence: 99%

Ethereal C–O Bond Cleavage Mediated by Ni(0)-Ate Complex: A DFT Study

et al. 2017

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Density functional theory calculations were performed to explore the mechanism of Ni-catalyzed crosscoupling reactions involving organo-lithium and -zinc reagents through ethereal C-O bond cleavage. Based on this work, together with our previous mechanistic study on etheric Kumada-Tamao reaction, we identify and characterize a novel catalytic cycle for cross-coupling mediated by Ni(0)-ate complex.Key words cross-coupling; ether; nickel catalyst; organolithium; organozinc; density functional theory (DFT) calculation Efficient and selective cleavage and transformation of C-O bonds, particularly by means of cross-coupling methods, has attracted great interest, since compounds containing C-O moieties occur widely in nature and are also extensively utilized in industry.1-8) Among C-O compounds, ethers are particularly attractive, [1][2][3][4][5][6][7][8] as they offer the advantages of 1) high atom economy/conversion efficiency (the use of ethers as simple as MeO as substrates affords fewer by-products compared with tosylate, mesylate, triflate, phosphate, etc.), 2) environmental compatibility (cleavage of the C-O moiety in ether releases non-halogen-containing waste), and 3) excellent stability, easy accessibility and wide diversity. However, ethereal C-O bonds ( E C-O) are very unreactive, and most of the well-established Pd-catalyzed C-O bond-cleaving protocols are ineffective for ethers.On the other hand, Ni-catalysts have proved effective for many types of C-O bond cleavage, including ethers. As early as in 1979, Wenkert et al. 9,10) reported the first Ni-catalyzed Kumada-Tamao type (Mg) 9-23) reaction, in which aryl methyl ether (ArOMe) acted as the electrophilic partner, and this is now recognized as the first example of Ni-catalyzed activation of an inert C-O bond. However, this breakthrough was overlooked for decades, until quite recently. After the development of improved conditions, ArOR can now be used as a coupling partner in several types of transition metal (TM)-catalyzed cross-couplings and related transformations, such as Suzuki-Miyaura-type (B), [24][25][26][27][28][29][30][31] Negishi-type (Zn or Al), [32][33][34][35][36] Murahashi-type (Li), [37][38][39][40] and other reactions. 41-50) As a continuation of our work in this area, we reported in 2012 the first ethereal Negishi-type coupling of aryl alkyl ether 36) (Chart 1(1)) and in 2016 we reported a systematic examination of ethereal Murahashi-type reaction 37) (Chart 1(2)). More recently, we also reported an in-depth study of Ni-catalyzed cross-coupling between organoaluminums and various types of C-O electrophiles, including aryl alkyl ether. 32) Results and DiscussionThe conventional catalytic cycle for cross-coupling reaction consists of three elemental steps: oxidative addition (OA), transmetalation, and reductive elimination. [51][52][53][54] Martin and colleagues reported that direct OA of a E C-O bond to Ni(0) requires high temperature, based on experimental and theoretical findings.46) Computational studies by Nakamura and colleagues, ...

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Nickel-induced conversion of carbon-oxygen into carbon-carbon bonds. One-step transformations of enol ethers into olefins and aryl ethers into biaryls

Cited by 372 publications

References 1 publication

Nickel(II) complexes with bifunctional phosphine–imidazolium ligands and their catalytic activity in the Kumada–Corriu coupling reaction

Nickel(II) complexes with bifunctional phosphine–imidazolium ligands and their catalytic activity in the Kumada–Corriu coupling reaction

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

Ethereal C–O Bond Cleavage Mediated by Ni(0)-Ate Complex: A DFT Study

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