- Fe(III)-catalyzed oxidative coupling of alkylnitriles with aromatic carboxylic acids: Facile access to cyanomethyl esters
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The first oxidative coupling of alkylnitriles with aromatic carboxylic acids using di-tert-butyl peroxide (DTBP) as oxidant was achieved under the catalysis of ionic Fe(III) complexes bearing an imidazolinium cation. This protocol features nontoxic iron catalysis, direct α-C(sp3)–H bond oxidative esterification of alkylnitriles, non-prefunctionalized starting materials, and a broad substrate scope with outstanding steric hindrance tolerance, providing a novel, straightforward, and green approach toward cyanomethyl ester synthesis.
- Wang, Dan,Lu, Bing,Song, Yan-Ling,Sun, Hong-Mei,Shen, Qi
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supporting information
(2019/08/01)
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- Conversion of oxazolines to cyanomethyl esters with pyridinium hydrobromide perbromide in water
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Various aromatic and heterocyclic oxazolines were directly converted to respective cyanomethyl esters with pyridinium hydrobromide perbromide in water at room temperature.
- Sayama, Shinsei
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p. 1133 - 1142
(2017/06/13)
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- Titanium-mediated addition of grignard reagents to acyl cyanohydrins: Aminocyclopropane versus 1,4-diketone formation
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The 1,2-dianion reactivity of the reagent generated from EtMgBr and titanium isopropoxide was illustrated when N-acyl cyanohydrins were used as substrates (>20 examples), giving both aminocyclopropane derivatives and 1,4-dicarbonyl compounds. When the reaction was performed in diethyl ether, 5-hydroxy-1,4-diketones were the main product. Under specific conditions (use of tetrahydrofuran and a bulky carboxylic moiety), the cyclopropane derivatives were obtained in good yields. The observed dichotomy may be explained by a ring-opening of the five-membered titanacycle intermediate followed by a nonselective acyl addition. The 1,2-dianion reactivity of the reagent generated from EtMgBr and Ti(OiPr)4 was illustrated when N-acyl cyanohydrins were used as substrates (>20 examples). When the reaction was performed in diethyl ether, 1,4-diketones were mainly isolated. Under certain conditions, cyclopropane derivatives were also obtained in good yields. A mechanism rationalizing this dichotomy is presented. Copyright
- Setzer, Paul,Forcher, Gwenael,Boeda, Fabien,Pearson-Long, Morwenna S. M.,Bertus, Philippe
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supporting information
p. 171 - 180
(2014/01/06)
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