BF3-catalyzed oxidative tandem annulation-aromatization of naphthols with terminal aryl alkenes

Liu, Long; Sun, Kang; Ji, Xuyu; Dong, Jianyu; Zhou, Yongbo; Yin, Shuang‐Feng

doi:10.1016/j.tet.2017.03.067

Cited by 7 publications

(1 citation statement)

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“…In 2013, Lei reported the first example of FeCl 3 -catalyzed coupling between phenols and styrene derivatives with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) as the terminal oxidant . Since then, many research groups, including those of Wang, Pappo, Yoon, and Chiba, have developed transition-metal-free, photochemical or electrochemical methods. ,, In 2016, Xia and co-workers applied this type of transformation to the total synthesis of (+)-decursivine, in which the key step involves an Fe-mediated intramolecular [3 + 2] oxidative cyclization to form the key [8.5]-ring system of the natural product . In addition, Canesi reported a related [3 + 2] cycloaddition between phenols and arenes and noted a stabilizing effect of a p -sulfone substituent on the phenol .…”

Section: C2 Functionalizationmentioning

confidence: 99%

Phenol-Directed C–H Functionalization

2018

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Phenols are important starting materials, intermediates, and functional elements of a very broad range of chemicals and materials. They are large-volume products of benzene oxidation and are increasingly available from biomass. Investment in methodologies that improve the efficiency of their use can have both immediate and future impacts on chemical upgrading. This review summarizes recent phenol-directed C–H functionalization reactions, which provide efficient increases in molecular complexity. Catalytic methodologies play an increasingly important role in addressing long-standing challenges of chemo- and regioselectivity, setting the stage for increased use of phenols in fine-chemical synthesis. We discuss these advances while underscoring persistent challenges, with the goal of motivating increased interest in this versatile functional group.

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Section: C2 Functionalizationmentioning

confidence: 99%

Phenol-Directed C–H Functionalization

2018

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Synthesis of Polysubstituted Naphthofurans and Indenofurans Based on a Regiodivergent Intramolecular Carbometalation Strategy with 2‐(2’‐Alkynylaryl)‐3‐iodofurans

Kondoh

Aita

Terada

2023

Chemistry A European J

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Efficient methods for the synthesis of two types of furan‐fused tricyclic compounds were developed based on a regiodivergent intramolecular carbometalation strategy using 2‐(2’‐alkynylaryl)‐3‐iodofurans as a common substrate. The iodine‐magnesium exchange/copper‐mediated 6‐endo‐anti intramolecular carbometalation sequence followed by nucleophilic substitution or palladium‐catalyzed cross‐coupling provided 2,3,4,5‐tetrasubstituted naphtho[1,2‐b]furans. On the other hand, the formal intramolecular 5‐exo‐anti carbopalladation/cross‐coupling sequence afforded 2,3‐disubstituted 4‐alkylidene‐4H‐indeno[1,2‐b]furans. The present methods provide new access to a wide range of well‐organized polysubstituted naphtho[1,2‐b]furans and indeno[1,2‐b]furans in a positional selective manner that are otherwise difficult to access.

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