One-step method for the synthesis of aryl olefins from aryl aldehydes and aliphatic aldehydes

Borate, Hanumant B.; Gaikwad, Supriya Hanmant; Kudale, Ananada S.; Pharande, Shrikant G.; Wagh, Vitthal D.; Sawant, Vikram S.

doi:10.1016/j.tetlet.2013.01.008

Cited by 5 publications

(1 citation statement)

References 23 publications

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“…5 mmHg) to give a clear, colorless oil (536 mg). Purification via bulb-to-bulb distillation under reduced pressure (160 °C ABT, 0.05 mmHg) gave 60 contaminated with ( E )-1-(4-methoxyphenyl)prop-1-ene (∼5%) as a clear, colorless oil (469 mg). Data for 60 : 1 H NMR (500 MHz, CDCl 3 ) 7.13 (d, J = 8.5 Hz, 2H), 6.86 (d, J = 8.5 Hz, 2H), 4.31–4.23 (m, 1H), 3.81 (s, 3H), 3.18 (dd, J = 14.1, 6.9 Hz, 1H), 3.02 (dd, J = 14.1, 7.2 Hz, 1H), 1.69 (d, J = 6.6 Hz, 3H).…”

Section: Experimental Sectionmentioning

confidence: 99%

Iron-Catalyzed Cross-Coupling of Unactivated Secondary Alkyl Thio Ethers and Sulfones with Aryl Grignard Reagents

2013

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The first systematic investigation of unactivated aliphatic sulfur compounds as electrophiles in transition metal-catalyzed cross-coupling are described. Initial studies focused on discerning the structural and electronic features of the organosulfur substrate which enable the challenging oxidative addition to the C(sp3)–S bond. Through extensive optimization efforts, an Fe(acac)3-catalyzed cross-coupling of unactivated alkyl aryl thio ethers with aryl Grignard reagents was realized, in which a nitrogen “directing group” on the S-aryl moiety of the thio ether served a critical role in facilitating the oxidative addition step. In addition, alkyl phenyl sulfones were found to be effective electrophiles in the Fe(acac)3-catalyzed cross-coupling with aryl Grignard reagents. For the latter class of electrophile, a thorough assessment of the various reaction parameters revealed a dramatic enhancement in reaction efficiency with an excess of TMEDA (8.0 equiv). The optimized reaction protocol was used to evaluate the scope of the method with respect to both the organomagnesium nucleophile and sulfone electrophile.

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Section: Experimental Sectionmentioning

confidence: 99%

Iron-Catalyzed Cross-Coupling of Unactivated Secondary Alkyl Thio Ethers and Sulfones with Aryl Grignard Reagents

2013

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Copper‐Catalyzed Intermolecular Hydroamination of Arylamines or Aza‐Heterocycles with Nitrostyrene Derivatives

2019

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A new copper-catalyzed protocol for the intermolecular anti-Markovnikov addition of arylamines or heterocycles to terminal and unsymmetrical 1,2-disubstituted vinylarenes has been developed. The direct hydroamination is catalyzed by a readily available N-heterocyclic carbene-based copper complex and KOt-Bu, and the use of MeOH as an additive enhances the reactivity. The method provides a broad range of new and versatile amine compounds bearing various functional groups in good to excellent yields. a] Reaction conditions: nitrostyrene 1 a (0.40 mmol), amine 2 (0.48 mmol), MeOH (0.40 mmol), IPrCuCl (5 mol%), KOt-Bu (5 mol%), toluene (1.0 M) under N 2 . [b] Yields of the isolated products. The reaction time was 7 h for 3 aa-3 ag and 12 h for 3 ah-3 aq.

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ChemInform Abstract: One‐Step Method for the Synthesis of Aryl Olefins from Aryl Aldehydes and Aliphatic Aldehydes.

et al. 2013

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Aliphatic Aldehydes. -The reaction of aromatic aldehydes with aliphatic ones in the presence of malononitrile proceeds via Knoevenagel products as intermediates (reaction mechanism). The mild conditions do not require a metal catalyst. AcOH can be replaced by proline or alanine with similar yields. -(BORATE*, H. B.; GAIKWAD, S. H.; KUDALE, A. S.; CHAVAN, S. P.; PHARANDE, S. G.; WAGH, V. D.; SAWANT, V. S.; Tetrahedron Lett. 54 (2013) 12, 1528-1530, http://dx.

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One-step method for the synthesis of aryl olefins from aryl aldehydes and aliphatic aldehydes

Cited by 5 publications

References 23 publications

Iron-Catalyzed Cross-Coupling of Unactivated Secondary Alkyl Thio Ethers and Sulfones with Aryl Grignard Reagents

Iron-Catalyzed Cross-Coupling of Unactivated Secondary Alkyl Thio Ethers and Sulfones with Aryl Grignard Reagents

Copper‐Catalyzed Intermolecular Hydroamination of Arylamines or Aza‐Heterocycles with Nitrostyrene Derivatives

ChemInform Abstract: One‐Step Method for the Synthesis of Aryl Olefins from Aryl Aldehydes and Aliphatic Aldehydes.

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