ortho-Induced transition-metal-free C-arylation cyclization reaction for the synthesis of polysubstituted isocoumarins

Liu, Lei; Hu, Jie; Wang, Xiang-Chuan; Zhong, Mei‐Jin; Liu, Xueyuan; Yang, Shang‐Dong; Liang, Yong‐Min

doi:10.1016/j.tet.2012.04.111

Cited by 32 publications

(14 citation statements)

References 46 publications

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“…To extend TMF arylation methods, Liu et al [16] developed the new protocol with the reactions of ortho-halo benzoicacid 11 and b-diketone 12 compounds in the presence of a base to form isocoumarines 13, 14. They employed halo aryl amides 15 which provided the desired product and intensive yields were observed (Scheme 4).…”

Section: Arylation Via Base Mediummentioning

confidence: 99%

Synthetic journey towards transition metal-free arylations

Roopan

Palaniraja

2014

Res Chem Intermed

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In general, aryl-aryl transformations were investigated via transition metal-catalysed reactions. However, transition metal-mediated organic synthesis provided higher yields but has some flaws such as high cost, and the need for careful exclusion of air and moisture during the reactions. Possibly, there may be contamination of the product from traces of heavy metals present. To overcome these kinds of disadvantages, continuous efforts have been focused on the recent development of aryl-aryl formation through transition metal-free (TMF) reactions. However, most of these cross-couplings reaction were limited to hetero and electron-rich arenes which require strong inorganic bases. Our critical review includes a synthetic pathway to prepared X-aryl (X = C, N, O and S) motif by a transition metal-free scenario. Formerly, TMF reactions were carried out by various sources like strong bases, diazodium salt, aryliodonium salt, organo-catalysts and versatile energy sources like microwave heating, visible light and photochemical reactor. In this review, we have focused on the transition metal-free arylations.

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Section: Arylation Via Base Mediummentioning

confidence: 99%

Synthetic journey towards transition metal-free arylations

Roopan

Palaniraja

2014

Res Chem Intermed

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“…The use of 2‐halobenzoic acids or their derivatives for Cu I ‐catalyzed coupling with 1,3‐diketones constitutes yet another good approach for the synthesis of 3‐arylisocoumarins;17 however, substrate availability limits the versatility of this route. The use of 2‐halobenzoic acids for arylation onto the activated methylene group of symmetrical β‐diketones under the influence of cesium carbonate as the base has also paved way for the synthesis of 3‐arylisocoumarins, but with unsymmetrical β‐diketones, the reaction yields a mixture of products 17e. The intramolecular version of the same reaction with 1‐(2‐halophenyl)‐3‐arylpropane‐1,3‐diones has also been successful 18.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of 3‐Arylisocoumarins by Using Acyl Anion Chemistry and Synthesis of Thunberginol A and Cajanolactone A

2015

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“…Only losing a molecule of water in the conversion, it concerns the concept of green chemistry in organic synthesis accordingly. In 2012, Liu's group realized this reaction under transition‐metal‐free conditions. However, the valuable 2‐iodobenzoic acid was used as a reactant (Scheme , (4)).…”

Section: Introductionmentioning

confidence: 91%