Vinylogous Elimination/Heck Coupling/Allylation Domino Reactions: Access to 2-Substituted 2,3-Dihydrobenzofurans and Indolines

Yang, Jianguo; Mo, Hanjie; Jin, Xiuxiu; Cao, Dongdong; Wu, Haijian; Chen, Di; Wang, Zhiming

doi:10.1021/acs.joc.7b02986

Cited by 15 publications

(4 citation statements)

References 58 publications

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“…Dihydrobenzofuran and indolines‐containing molecules are very important heterocyclic compounds that are found in numerous bioactive natural products and pharmaceuticals. In 2018, Yang [42] and his research group described the preparation of 2‐ substituted 2,3‐dihydrobenzofurans 58 and Indolines 61 through highly regio and stereoselective Pd catalyzed elimination/intermolecular domino Heck reaction of functionalized aryl allyl ethers 55 and halo phenols 54 as precursors (Scheme 11). Synthesis of heterocyclic frameworks from various aryl allyl ethers is difficult because of their high stabilities in metal‐catalyzed domino Heck reactions.…”

Section: Transition‐metal Catalyzed Domino‐ Cyclization For Heterocyc...mentioning

confidence: 99%

Recent Advances in Transition Metal‐Catalyzed Domino‐Cyclization Strategies for Functionalized Heterocyclic/Carbocyclic Compounds

et al. 2022

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The discovery of the Domino reaction offers a useful strategy to the scientific community. From the beginning, it has received much attention in numerous advances for organic synthesis. Especially, for the constructive cyclization via multiple C−C and C‐heteroatom bond formation, the Domino‐Heck coupling reaction has become an essential tool in organic chemistry. In the case of drug synthesis, different natural products and biologically relevant scaffolds are achieved by employing the Domino‐cyclization technique. Palladium or nickel‐based intramolecular coupling reactions have been associated with many developing methods which lead to important carbo or heterocyclic scaffolds. In this account, metal‐catalyzed intramolecular cyclization is an emerging tool to access several heterocyclic scaffolds such as coumarins, quinolines, piperidines, indoles spiro and fused polycyclic rings. In this review, we have attempted to highlight the recent advances in metal‐mediated Domino cyclization reaction over the past few years.

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Section: Transition‐metal Catalyzed Domino‐ Cyclization For Heterocyc...mentioning

confidence: 99%

Recent Advances in Transition Metal‐Catalyzed Domino‐Cyclization Strategies for Functionalized Heterocyclic/Carbocyclic Compounds

et al. 2022

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“…In 2018, Yang, Wang, and co-workers reported that o-iodophenols underwent a highly regio-and stereoselective palladium-catalyzed domino reaction with functionalized aryl allyl ethers to give 2-vinyl-DHBs (Scheme 18). 66 Various aryl allyl ethers were easily prepared by the phosphine-catalyzed addition of electrondeficient allenes with phenol and were efficient substrates for the synthesis of 2-substituted DHBs.…”

Section: Scheme 17 22-difluoro-3-hydroxy-dhb From Salicylaldehydes Amentioning

confidence: 99%

Recent Advances in Synthetic Strategies to 2,3-Dihydrobenzofurans

Laurita

D’Orsi²,

Chiummiento³

et al. 2020

Synthesis

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This review gives an overview on recent developments in methods for the construction of compounds with the 2,3-dihydrobenzofuran core in the period 2012 to 2019. Interest in 2,3-dihydrobenzofurans is constantly increasing. The methods are divided into intermolecular and intramolecular approaches. Intermolecular approaches are subdivided according to the parent intermediate for the key reaction, while intermolecular approaches are subdivided according by which bond is formed in the key reaction. The transformation of benzofurans to dihydrobenzofurans and other miscellaneous methods are also discussed. Approaches useful for the synthesis of natural products are emphasized.1 Introduction2 Intermolecular Approaches2.1 o-Quinone Methides and o-Quinones2.2 p-Quinone Methides and p-Quinones2.3 Nitrogen-Containing Phenols and Quinones2.4 o-Hydroxyphenylcarbonyl Derivatives and Phenols2.5 Miscellaneous3 Intramolecular Approaches3.1 O–C2 Bond Forming3.2 C2–C3 Bond Forming3.3 C3–Aryl Bond Forming3.4 O–Aryl Bond Forming4 From BF to DHB5 Rearrangements and Aromatizations

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“…With the aim to increase the reaction scope of the heteroannulations of 1,3-dienes and 2-iodoanilines, Wang, Yang, and co-workers reported the synthesis of 2-vinylindolines 45 using 2-iodo-N-tosylanilines and electrondeficient allyl ethers 44 as a diene surrogate (Scheme 15). 18 In particular, the use of NaHCO 3 as base promoted the vinylogous elimination of the phenoxy group on the starting allyl ether to provide the correspondent aryl diene. Subsequent intermolecular Heck coupling/intramolecular allylation afforded the substituted 1-tosyl-2-vinylindolines 45.…”

Section: Scheme 14 2-(2-ethoxyvinyl)indolines By Regioselective Hetermentioning

confidence: 99%

Pd-Catalyzed Domino Reactions Involving Alkenes To Access Substituted Indole Derivatives

et al. 2020

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Palladium-catalyzed domino reactions are advanced tools in achieving various nitrogen-containing heterocycles in an efficient and economical manner due to the reduced number of steps in the process. This review highlights recent advances in domino processes aimed at the synthesis of indole derivatives and polycyclic systems containing the indole nucleus in intra/intra- or intra/intermolecular reactions. In particular, we consider domino processes that involve a double bond in a step of the sequence, which allow the issue of regioselectivity in the cyclization to be faced and overcome. The different sections in this review focus on the synthesis of the indole nucleus and functionalization of the scaffold starting from different substrates that have been identified as activated starting materials, which involve a halogenated moiety or unactivated unsaturated systems. In the former case, the reaction is under Pd(0) catalysis, and in the second case a Pd(II) catalytic species is required and then an oxidant is necessary to reconvert the Pd(0) into the active Pd(II) species. On the other hand, the second method has the advantage that it uses easy available and inexpensive substrates.1 Introduction2 Indole Scaffold Synthesis2.1 Activated Substrates2.2 Unactivated Substrates3 Functionalization of Indole Scaffold3.1 Activated Substrates3.2 Unactivated Substrates4 Conclusions

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Vinylogous Elimination/Heck Coupling/Allylation Domino Reactions: Access to 2-Substituted 2,3-Dihydrobenzofurans and Indolines

Cited by 15 publications

References 58 publications

Recent Advances in Transition Metal‐Catalyzed Domino‐Cyclization Strategies for Functionalized Heterocyclic/Carbocyclic Compounds

Recent Advances in Transition Metal‐Catalyzed Domino‐Cyclization Strategies for Functionalized Heterocyclic/Carbocyclic Compounds

Recent Advances in Synthetic Strategies to 2,3-Dihydrobenzofurans

Pd-Catalyzed Domino Reactions Involving Alkenes To Access Substituted Indole Derivatives

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