McMurry intermolecular cross-coupling between an ester and a ketone: scope and limitations

Sabelle, Stéphane; Hydrio, Jérôme; Leclerc, E.; Mioskowski, Charles; Renard, Pierre

doi:10.1016/s0040-4039(02)00617-2

Cited by 42 publications

(12 citation statements)

References 16 publications

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“…(−)-Fenchone showed to be not reactive in HWE conditions, independent of the base used (NaH, n-BuLi, sec-BuLi, LDA, LiHMDS), with no product formation detected at all, even after a 24 h reaction time. Also, the intermolecular McMurry cross-coupling 15,25 of methyl 3-methoxybenzoate and (−)-fenchone, in the presence of either TiCl 3 /LiAlH 4 /TEA or TiCl 4 /Zn, did not produce reproducible results. 26 The attribution of NMR signals and quantification of the E and Z isomers of 1a and 1b was performed as follows.…”

Section: Resultsmentioning

confidence: 94%

Synthesis of some fenchyl-substituted alkenes and enol-ethers containing 3-oxyphenyl substituents by the Barton-Kellogg reaction

Ciscato¹,

Bastos²,

Bartoloni

et al. 2010

J. Braz. Chem. Soc.

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Usando-se a reação de Barton-Kellogg, foram sintetizados um alceno e dois enóis-éteres fenchyl-substituídos, contendo grupos 3-oxifenila como substituintes. O fenchil-alceno aromático tri-substituído 1a foi preparado com rendimento de 53% a partir de tiofenchona e um diazoanisol. A abordagem inversa, baseada no acoplamento entre diazofenchona e tionoésteres aromáticos, foi utilizada para produzir os enóis-éteres 1b e 1c (rendimentos 95 e 75%, respectivamente). Em todos os casos foi obtida uma mistura dos isômeros E e Z; a atribuição e quantificação destes isômeros foram realizadas pela análise dos dados de espectroscopia de RMN assistida por cálculos teóricos (relação E/Z 1a = 0,72, 1b = 2,2, 1c = 1,8). A reação ocorre com baixa estereosseletividade, levando à formação preferencial dos diastereoisômeros das olefinas e enóis-éteres, nos quais o substituinte aromático está localizado ao lado dos dois grupos metila da porção fenchila.The synthesis of one fenchyl-substituted alkene and two enol-ethers, containing 3-oxyphenyl substituents by the Barton-Kellogg reaction is described. The tri-substituted aromatic fenchylalkene 1a was prepared in 53% yield from thiofenchone and a diazoanisole; whereas enol-ethers 1b and 1c were obtained (95 and 75% yield, respectively) using an inverse approach based on diazofenchone and aromatic thionoesters. A mixture of Z and E isomers was obtained in all cases; isomer attribution and quantification has been carried out by analysis of NMR spectroscopic data assisted by theoretical calculations (E/Z ratio: 1a = 0.72, 1b = 2.2, 1c = 1.8). Reaction proceeds with low stereoselectivity leading to the preferential formation of diastereoisomeric olefins and enol-ethers where the aromatic substituent resides at the side of the two fenchyl methyl groups.

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Section: Resultsmentioning

confidence: 94%

Synthesis of some fenchyl-substituted alkenes and enol-ethers containing 3-oxyphenyl substituents by the Barton-Kellogg reaction

Ciscato¹,

Bastos²,

Bartoloni

et al. 2010

J. Braz. Chem. Soc.

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“…The TiCl 3 -LiAlH 4 system in the presence of NEt 3 is the most efficient reagent for keto-ester cross coupling reactions [96][97][98]. Renard et al [98] recently reported on the scope and limitations of intermolecular McMurry cross-coupling reaction between a benzylic ester and a hindered ketone.…”

Section: Mcmurry Coupling Reactionmentioning

confidence: 99%

“…Renard et al [98] recently reported on the scope and limitations of intermolecular McMurry cross-coupling reaction between a benzylic ester and a hindered ketone. Using TiCl 3 (10 equiv)-LiAlH 4 (5 equiv)-Et 3 N (6 equiv) in THF at 70˚C and slow addition of both carbonyl compounds, a simple 1.2 excess of 2-adamantanone over tert-butyl- [73,99].…”

Section: Mcmurry Coupling Reactionmentioning

confidence: 99%

Low-Valent Titanium-Mediated Reductive Coupling of Carbonyl Compounds

Ladipo¹

2006

COC

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This account describes recent organic synthesis applications and developments in mechanistic understanding of low-valent titanium-mediated reductive coupling of carbonyl compounds. Pinacol and McMurry coupling reactions are among the most powerful methods for constructing carbon-carbon bonds, and have served as the key step in the synthesis of various natural and synthetic products. The range and selectivity of low-valent titanium reagents that mediate pinacol and McMurry reactions are discussed. The nature of their active species is discussed in conjunction with relevant chemistry of well-characterized low-valent titanium complexes, all of which serve to inform current understanding of the reaction mechanisms.

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“…[16][17][18] Sterically hindered and spiro-substituted olefins can be prepared by several methods; including dehydration, McMurry, and Horner-Wadsworth-Emmons couplings (Scheme 2). 6,15,[19][20][21]…”

Section: Scheme 1 Chemiluminescence Of Aromatic Spiroadamantylmentioning

confidence: 99%

Comparison of Convenient Alternative Synthetic Approaches to 4-[(3-tert-Butyldimethylsilyloxy)phenyl]-4-methoxyspiro[1,2-dioxetane-3,2′-adamantane]

Bastos¹,

Ciscato²,

Weiss³

et al. 2006

Synthesis

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The preparation of 4-(3-tert-butyldimethylsilyloxyphenyl)-4-methoxyspiro[1,2-dioxetane-3,2¢-adamantane] by two different approaches is described and the results are compared with previously reported data. The precursor olefin, 1-[3-(tert-butyldimethylsilyloxy)phenyl]-1-methoxy-2-spiroadamantylidene is obtained from 3-hydroxybenzaldehyde by both Horner-WadsworthEmmons and McMurry coupling reactions in 42% overall yield in both cases. 1,2-Dioxetane preparation by singlet oxygen addition, obtained through calcium peroxide diperoxohydrate thermolysis, is compared with conventional photooxygenation.

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McMurry intermolecular cross-coupling between an ester and a ketone: scope and limitations

Cited by 42 publications

References 16 publications

Synthesis of some fenchyl-substituted alkenes and enol-ethers containing 3-oxyphenyl substituents by the Barton-Kellogg reaction

Synthesis of some fenchyl-substituted alkenes and enol-ethers containing 3-oxyphenyl substituents by the Barton-Kellogg reaction

Low-Valent Titanium-Mediated Reductive Coupling of Carbonyl Compounds

Comparison of Convenient Alternative Synthetic Approaches to 4-[(3-tert-Butyldimethylsilyloxy)phenyl]-4-methoxyspiro[1,2-dioxetane-3,2′-adamantane]

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