Facile stereoselective syntheses of aryl substituted α,β‐unsaturated esters containing a trifluoromethyl group

Pan, Rui-Qi; Wang, Pingan; Deng, Min‐Zhi

doi:10.1002/hc.10032

Cited by 5 publications

(2 citation statements)

References 20 publications

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“…Ethyl ( E )-4,4,4-trifluoro-3-(4-methylphenyl)but-2-enoate , (Table , entries 12−15) was synthesized from 4-(trifluoroacetyl)toluene ( m ). 1 H NMR (300 MHz, CDCl 3 ): δ 7.19 (s, 4H), 6.58 (q, 1H, J = 1.5 Hz), 4.06 (q, 2H, J = 7.2 Hz), 2.37 (s, 3H), 1.09 (t, 3H, J = 7.2 Hz).…”

Section: Methodsmentioning

confidence: 99%

General and Selective Olefination of Aldehydes and Ketones Catalyzed by a Cobalt(II) Porphyrin Complex

2003

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The Co(II) porphyrin complex Co(TPP) is an efficient and versatile catalyst for selective olefination of carbonyl compounds, including aldehydes and activated and unactivated ketones, with ethyl diazoacetate (EDA) in the presence of triphenylphosphine. The catalytic reactions of aldehydes and activated ketones can be carried out in a one-pot fashion with the use of a stoichiometric amount of diazo reagents, affording olefins in high yields and high E selectivity. In the case of unactivated ketones, a substoichiometric amount of benzoic acid is required to promote the catalytic reactions.

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Section: Methodsmentioning

confidence: 99%

General and Selective Olefination of Aldehydes and Ketones Catalyzed by a Cobalt(II) Porphyrin Complex

2003

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“…Ethyl ( E )-4,4,4-Trifluoro-3-(4-methylphenyl)but-2-en-oate (2) was synthesized from 4-(trifluoroacetyl)toluene. 1 H NMR (300 MHz, CDCl 3 ): δ 7.19(s, 4H), 6.58(q, 1H, J = 1.5 Hz), 4.06(q, 2H, J = 7.2 Hz), 2.37(s, 3H), 1.09(t, 3H, J = 7.2 Hz).…”

Section: Methodsmentioning

confidence: 99%

Efficient and Stereoselective Synthesis of β-Trifluoromethyl α,β-Unsaturated Esters via Iron(III) Porphyrin-Catalyzed Olefination of Ketones

2003

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beta-Trifluoromethyl alpha,beta-unsaturated esters were efficiently prepared by reactions of fluorine-containing ketones with diazo compounds via metalloporphyrin-catalyzed olefination in the presence of triphenylphosphine. The commercially available Fe(III)(TPP)Cl (TPP: tetraphenylporphyrin) is effective for catalyzing the olefination of a variety of trifluoromethyl ketones with different diazoacetate esters under mild conditions. The reactions proceeded with high yields (up to 95% isolated yield) and high stereoselectivity (up to 99% (E)-selectivity).

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Synthesis and Application of gem‐Difluoromethylenated and Trifluoromethylated Building Blocks

Qing

Qiu²

2012

Efficient Preparations of Fluorine Compounds

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Facile stereoselective syntheses of aryl substituted α,β‐unsaturated esters containing a trifluoromethyl group

Abstract: The Suzuki-type cross-coupling reaction of arylboronic acids 3 with ethyl (Z)-3-iodo-4,4,4-trifluoro-2-butenoate 2, which was generated by hydroiodination of available ethyl 4,4,4-trifluoro-2-butynoate 1, to afford ethyl (E)-3-aryl-4,4,4-trifluoro-

Cited by 5 publications

References 20 publications

General and Selective Olefination of Aldehydes and Ketones Catalyzed by a Cobalt(II) Porphyrin Complex

General and Selective Olefination of Aldehydes and Ketones Catalyzed by a Cobalt(II) Porphyrin Complex

Efficient and Stereoselective Synthesis of β-Trifluoromethyl α,β-Unsaturated Esters via Iron(III) Porphyrin-Catalyzed Olefination of Ketones

Synthesis and Application of gem‐Difluoromethylenated and Trifluoromethylated Building Blocks

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