Transition-Metal-Free C-Arylation at Room Temperature by Arynes

Dhokale, Ranjeet A.; Thakare, P.; Mhaske, Santosh B.

doi:10.1021/ol301768r

Cited by 43 publications

(15 citation statements)

References 54 publications

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“…Chemoselective a-arylation of b-bica-rbonyl compounds (malonamide esters) 46 and 48 using aryne 35-49 intermediates via fluoride-promoted TMF conditions at room temperature have been developed by Dhokale et al [23]. Similar work has been reported via a transition metal-catalysed reaction.…”

Section: Arylation Via Aryne Intermediatementioning

confidence: 86%

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 Aryne Intermediatementioning

confidence: 86%

Synthetic journey towards transition metal-free arylations

Roopan

Palaniraja

2014

Res Chem Intermed

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“…Over the past century, several important advances in the area of aromatic nitration have been reported (Figure ). − In continuation of our research interest in the development of novel and original methodologies using arynes as reactive intermediates, we were curious to see whether an alternative protocol using simple reagents and mild reaction conditions could be developed for the synthesis of nitroaromatics by hitherto unknown nucleophilic nitration of arynes. Herein we present our results on the outcome of our envisioned transformation and its application in a multicomponent reaction.…”

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confidence: 99%

Nucleophilic Nitration of Arynes by Sodium Nitrite and its Multicomponent Reaction Leading to Double-Functionalized Arenes

Dhokale

Mhaske

2016

Org. Lett.

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An unusual nucleophilic nitration of arynes by NaNO2 in the presence of water has been developed, and the concept was further demonstrated to accomplish a double functionalization of arynes using a multicomponent reaction protocol to synthesize pharmaceutically important (2-nitrophenyl)methanol derivatives. Such substitution ortho to -NO2 is difficult by other means. The reaction conditions are mild and avoid the use of strong acids, expensive transition metal catalysts, and additives.

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“…Our group has been engaged in the development of novel and useful methodologies in aryne chemistry, which prompted us to apply it in the construction of leptosphaerin C core and its analogues. Such applications of arynes generated by various ways, in particular by Kobayashi’s method, to synthesize key intermediates in the total synthesis of natural products is gaining importance .…”

Section: Introductionmentioning

confidence: 99%

Diversity-Oriented Synthesis of Spiroannulated Benzofuran-3-one Scaffold of Leptosphaerin C and Congeners via Aryne Insertion

Dhokale

Mhaske

2017

J. Org. Chem.

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A concise synthesis of functionalized cyclohexenone-fused spirobenzofuran-3-ones under mild reaction conditions was developed. The reaction proceeds via insertion of aryne into the C-O bond followed by a regioselective intramolecular conjugate addition. The use of silyl-protected acid was crucial for the transformation. This protocol was successfully applied for the synthesis of leptosphaerin C core and its novel analogues.

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Transition-Metal-Free C-Arylation at Room Temperature by Arynes

Cited by 43 publications

References 54 publications

Synthetic journey towards transition metal-free arylations

Synthetic journey towards transition metal-free arylations

Nucleophilic Nitration of Arynes by Sodium Nitrite and its Multicomponent Reaction Leading to Double-Functionalized Arenes

Diversity-Oriented Synthesis of Spiroannulated Benzofuran-3-one Scaffold of Leptosphaerin C and Congeners via Aryne Insertion

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