- Metal-free [3 + 2 + 1] annulation of allylic alcohols, ketones, and ammonium acetate: radical-involving synthesis of 2,3-diarylpyridine derivatives
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A three-component [3 + 2 + 1] annulation strategy for the synthesis of biologically and pharmaceutically active 2,3-diarylpyridine derivatives by using a series of allylic alcohols, ketones, and ammonium acetate as substrates has been developed. The method proceeds efficiently under metal-free conditions, and the desired heterocycles could be obtained in a site-specific selectivity manner with good functional group tolerance.
- Ge, Danhua,Luo, Xin-Long,Tang, Xi,Pang, Chao-Bin,Wang, Xin,Chu, Xue-Qiang
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supporting information
p. 2277 - 2283
(2021/03/24)
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- Reinventing the de Mayo reaction: Synthesis of 1,5-diketones or 1,5-ketoesters via visible light [2+2] cycloaddition of β-diketones or β-ketoesters with styrenes
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A visible light mediated De Mayo reaction between 1,3-diketones and styrenes following a [2+2] cycloaddition pathway via a photosensitization mechanism gives access to 1,5-diketones. The reaction has been applied to substituted styrenes and aryl- and alkyl-substituted ketones. Moreover, the method converts β-ketoesters, β-amido esters, and β-cyano ketones. Seven membered rings, a frequent structural motif of natural products, are also accessible using this methodology.
- Martinez-Haya, Rebeca,Marzo, Leyre,K?nig, Burkhard
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p. 11602 - 11605
(2018/10/31)
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- Metal-free oxidative radical addition of carbonyl compounds to a,a-Diaryl allylic alcohols: Synthesis of highly functionalized Ketones
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A metal-free direct alkylation of simple carbonyl compounds (ketones, esters, and amides) with a,a-diaryl allylic alcohols is described. The protocol provides facile access to highly functionalized dicarbonyl ketones by a radical addition/1,2-aryl migration cascade. The regioselectivity of the reaction was precisely controlled by the nature of the carbonyl compound.
- Chu, Xue-Qiang,Meng, Hua,Zi, You,Xu, Xiao-Ping,Ji, Shun-Jun
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supporting information
p. 17198 - 17206
(2015/01/09)
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- Photocycloaddition of Some Difluoro(aminoenonato)boron Complexes with Arylalkenes
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The photocycloaddition of some difluoro [(methylamino- κ N)alkenonato-κO]boron complexes 1 with arylalkenes 2 is discussed. The resulting [2 + 2] photoaddition gave the cyclobutane and azetidine derivatives (Schemes 1, 3, and 5). Rearrangements of the cyclobutane gave 1,5-diketones derivatives (Schemes 2, 4, and 5). The yields of the photoadducts were governed by the reduction and oxidation potentials. Furthermore, the configurations of the products established high regio- and stereoselectivity, suggesting the presence of a singlet exciplex. The reactivity and the stereochemistry were rationalized by means of FMO (frontier molecular orbital) calculations.
- Itoh, Kuniaki,Okazaki, Kazuhiko,Chow, Yuan L.
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p. 292 - 302
(2007/10/03)
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