Copper-Mediated, Palladium-Catalyzed Cross-Coupling of 3-Iodochromones, Thiochromones, and Quinolones with Ethyl Bromodifluoroacetate

Han, Xiaodong; Yue, Zhizhou; Zhang, Xiaofei; He, Qian; Yang, Chunhao

doi:10.1021/jo400412k

Cited by 46 publications

(18 citation statements)

References 43 publications

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“…Although some synthetic approaches to thiochroman-4-ones, thioflavone, and thiochromones have been reported in literature [ 28 , 39 , 40 , 41 , 42 , 43 , 44 , 45 , 46 , 47 , 48 , 49 , 50 , 51 , 52 , 53 , 54 , 55 ], research on efficient synthesis of 2-substituted thiochroman-4-ones is an underexplored area when compared to O-containing counterparts. Synthetic approaches to 2-substituted thiochroman-4-ones utilizing Friedel-Crafts acylation of thiopropanoic acid [ 56 ], hydrogenation of thiochromones [ 57 , 58 , 59 ], and intramolecular thio-Michael addition [ 60 , 61 , 62 , 63 , 64 , 65 , 66 ] have been reported.…”

Section: Introductionmentioning

confidence: 99%

Development of Conjugate Addition of Lithium Dialkylcuprates to Thiochromones: Synthesis of 2-Alkylthiochroman-4-ones and Additional Synthetic Applications

et al. 2018

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Lithium dialkylcuprates undergo conjugate addition to thiochromones to afford 2-alkylthiochroman-4-ones in good yields. This approach provide an efficient and general synthetic approach to privileged sulfur-containing structural motifs and valuable precursors for many pharmaceuticals, starting from common substrates-thiochromones. Good yields of 2-alkyl-substituted thiochroman-4-ones are attained with lithium dialkylcuprates, lithium alkylcyanocuprates or substoichiometric amount of copper salts. The use of commercially available inexpensive alkyllithium reagents will expedite the synthesis of a large library of 2-alkyl substituted thiochroman-4-ones for additional synthetic applications.

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Section: Introductionmentioning

confidence: 99%

Development of Conjugate Addition of Lithium Dialkylcuprates to Thiochromones: Synthesis of 2-Alkylthiochroman-4-ones and Additional Synthetic Applications

et al. 2018

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“…In 2013, in the course of the development of novel anticancer agents, Yang and co‐workers carried out the palladium‐catalyzed ethoxycarbonyldifluoromethylation of 3‐iodochromones, thiochromones, and 4‐quinolones 9 a – j (Scheme ) 12. The reaction in the presence of Pd(dppf)Cl 2 as a catalyst, ethyl bromodifluoroacetate, and an excess of copper metal afforded the difluoromethylated products 10 a – j in moderate to excellent yields.…”

Section: Introduction Of Functionalized Fluorinated Building Blocks Omentioning

confidence: 99%

Recent Progress toward the Introduction of Functionalized Difluoromethylated Building Blocks onto C(sp²) and C(sp) Centers

Belhomme

Besset

Poisson

et al. 2015

Chemistry A European J

313

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Fluorine chemistry is a field undergoing tremendous expansion. Although much attention has been paid to the introduction of the fluorine atom and the CF3 group, less interest has been devoted to the introduction of functionalized fluorinated building blocks, in sharp contrast with the high versatility of the fluorinated products. In this Minireview, the most relevant methods for the introduction of difluoromethylated building blocks are summarized. Access to difluoromethylated arenes, alkenes, and alkynes is highlighted and special attention is paid to explanation of the reaction mechanism.

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“…In both species, two different transcripts derived from the same coding region have been described. [7][8][9][10][11][12][13] A variety of synthetic strategies have been developed for the synthesis of 4-quinolones. 3 Each monomer contains three metallic ions (two zinc molecules and one of magnesium) and one phosphate ion.…”

Section: Introductionmentioning

confidence: 99%

Diversity oriented synthesis of 6-nitro- and 6-aminoquinolones and their activity as alkaline phosphatase inhibitors

et al. 2015

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During the optimization of the conditions of the cyclization, we were able to isolate sideproducts 9 and 10 (Scheme 2). The quantity of these compounds strongly depends on the conditions (see legend of Table 2). The formation of products 9 can be explained by reaction of 6 with two molecules of the amine, i.e. conjugate addition to the ynone and nucleophilic substitution at the arene. Products 10 are formed by conjugate addition of the amine to the alkynone moiety. Under the standard conditions applied for the synthesis of quinolones 7, sideproducts 9 and 10 were formed only in very small quantities (1-2%). However, 9a-d could be isolated and spectroscopically characterized when the reaction was carried out at lower temperature. Reduction of the reaction time during the synthesis of nitroquinolone derivatives allowed us to isolate intermediates 10a and 10b. In general, the yields of unwanted side-products 9 and 10 increased when potassium fluoride was employed instead of standard K 2 CO 3 and K 3 PO 4 . Scheme 2. Side-products 9 and 10. Yields of isolated compounds obtained in reaction conditions specified in footnotes g, h, and i of Table 2.

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Copper-Mediated, Palladium-Catalyzed Cross-Coupling of 3-Iodochromones, Thiochromones, and Quinolones with Ethyl Bromodifluoroacetate

Cited by 46 publications

References 43 publications

Development of Conjugate Addition of Lithium Dialkylcuprates to Thiochromones: Synthesis of 2-Alkylthiochroman-4-ones and Additional Synthetic Applications

Development of Conjugate Addition of Lithium Dialkylcuprates to Thiochromones: Synthesis of 2-Alkylthiochroman-4-ones and Additional Synthetic Applications

Recent Progress toward the Introduction of Functionalized Difluoromethylated Building Blocks onto C(sp²) and C(sp) Centers

Diversity oriented synthesis of 6-nitro- and 6-aminoquinolones and their activity as alkaline phosphatase inhibitors

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Copper-Mediated, Palladium-Catalyzed Cross-Coupling of 3-Iodochromones, Thiochromones, and Quinolones with Ethyl Bromodifluoroacetate

Cited by 46 publications

References 43 publications

Development of Conjugate Addition of Lithium Dialkylcuprates to Thiochromones: Synthesis of 2-Alkylthiochroman-4-ones and Additional Synthetic Applications

Development of Conjugate Addition of Lithium Dialkylcuprates to Thiochromones: Synthesis of 2-Alkylthiochroman-4-ones and Additional Synthetic Applications

Recent Progress toward the Introduction of Functionalized Difluoromethylated Building Blocks onto C(sp2) and C(sp) Centers

Diversity oriented synthesis of 6-nitro- and 6-aminoquinolones and their activity as alkaline phosphatase inhibitors

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Recent Progress toward the Introduction of Functionalized Difluoromethylated Building Blocks onto C(sp²) and C(sp) Centers