Direct Assembly of 3,4‐Difunctionalized Benzofurans and Polycyclic Benzofurans by Phenol Dearomatization and Palladium‐Catalyzed Domino Reaction

Han, Zhaomeng; Zhang, Liang; Li, Zhiming; Fan, Renhua

doi:10.1002/anie.201404155

Cited by 45 publications

(14 citation statements)

References 53 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…In connection with our recent research on the synthesis of 3,4‐difunctionalized benzofurans from 2‐alkynylphenols,10 we focused our attention on developing methods that directly convert 2‐alkynylanilines into 3,4‐fused indoles 11. For a medicinal chemistry project, we were interested in the synthesis of oxocino[4,3,2‐ cd ]indoles ( 3 ) because of their structural similarity to many natural products and potential biological activities 12…”

Section: Methodsmentioning

confidence: 99%

Aniline Dearomatization and Silver‐Catalyzed [3+3] Dipolar Cycloaddition: Efficient Construction of Oxocino[4,3,2‐cd]indoles from 2‐Alkynylanilines and 2‐Alkynylbenzaldoximes

Han

Fan

2015

Angewandte Chemie

Self Cite

View full text Add to dashboard Cite

2-Alkynylanilines are attractive starting materials in indole synthesis because of their ready availability.H erein, ao ne-pot stepwise procedure is reported for efficient construction of multisubstituted oxocino[4,3,2-cd]indoles from 2alkynylanilines and 2-alkynylbenzaldoximes.T he method comprises the oxidative dearomatization of 2-alkynylanilines, the silver-catalyzed [3+ +3] cycloaddition with 2-alkynylbenzaldoximes,a nd subsequent thermal radical skeletal rearrangement and aromatization.

show abstract

Section: Methodsmentioning

confidence: 99%

Aniline Dearomatization and Silver‐Catalyzed [3+3] Dipolar Cycloaddition: Efficient Construction of Oxocino[4,3,2‐cd]indoles from 2‐Alkynylanilines and 2‐Alkynylbenzaldoximes

Han

Fan

2015

Angewandte Chemie

Self Cite

View full text Add to dashboard Cite

show abstract

“…[23] The general synthetic strategies to construct the valuable benzofurans motifs mainly rely on the assembly of a substituted furan framework on a benzenoid scaffold through an intramolecular annulation. [24] In 2017, Huang and co-workers reported a simple, unique, and efficient phosphine-mediated benzannulation reaction of acyclic enynone substrates 27 by an intermolecular approach. [25] When the formylchromones 28 with 27 were used as substrates, the corresponding benzannulation products 29 were obtained in good to excellent yields.…”

Section: Phosphine-mediated Benzannulation Reactionsmentioning

confidence: 99%

Recent Advances in Organocatalyst‐Mediated Benzannulation Reactions

2020

Adv Synth Catal

View full text Add to dashboard Cite

Aromatic compounds are omnipresent in organic chemistry, which are the broadest skeletons of bioactive molecules, medicines, and materials. Due to their importance, conventional methods to assemble aromatic rings have attracted considerable attention. The direct formation of benzene cores from readily available acyclic precursors offers a highly versatile and superior approach to prepare both small organic molecules and sophisticated natural products. Recently, organocatalyst-mediated annulation reaction, including phosphine-, tertiary amine-, secondary amine-, primary amine-, and NHC-mediated benzannulation reactions, is considered as an efficient method to access multi-substituted arenes. In this review, we will emphasize the selected examples of organocatalyst-mediated benzannulation reactions of available acyclic precursors for the construction of diverse aromatics.

show abstract

“…Synthesis of 10 H ‐indeno[1,2‐ b ]benzofuran‐9‐amine derivatives from 2‐((2‐alkenylphenyl)ethynyl)phenols, through the formation of 4‐methoxy‐2‐((2‐alkenylphenyl)ethynyl)cyclohexa‐2,5‐dien‐1‐ones as synthetic intermediates …”

Section: Pd(ii)‐catalyzed Processesmentioning

confidence: 99%

Palladium‐Catalyzed Double Cyclization Processes Leading to Polycyclic Heterocycles: Recent Advances

et al. 2019

View full text Add to dashboard Cite

In this minireview, we discuss some recently reported methods for the synthesis of polycyclic heterocycles by palladium‐catalyzed double cyclization processes. Paradigmatic examples taken by the most recent literature (from 2014 to the beginning of 2019) are presented. Only transformations in which palladium is involved in at least one cyclization stage are taken into consideration. The first part deals will Pd(0)‐catalyzed processes. Double cyclizations initiated by the oxidative addition of an Ar–X bond or other functional groups are treated first, followed by processes beginning with carbopalladation by Pd(0) attack to unsaturated bonds. The second part concerns Pd(II)‐catalyzed reactions, and begins with double cyclizations initiated by intramolecular nucleophilic attack to unsaturated bonds coordinated to Pd(II), followed by processes initiated by aromatic palladation.

show abstract

Direct Assembly of 3,4‐Difunctionalized Benzofurans and Polycyclic Benzofurans by Phenol Dearomatization and Palladium‐Catalyzed Domino Reaction

Cited by 45 publications

References 53 publications

Aniline Dearomatization and Silver‐Catalyzed [3+3] Dipolar Cycloaddition: Efficient Construction of Oxocino[4,3,2‐cd]indoles from 2‐Alkynylanilines and 2‐Alkynylbenzaldoximes

Aniline Dearomatization and Silver‐Catalyzed [3+3] Dipolar Cycloaddition: Efficient Construction of Oxocino[4,3,2‐cd]indoles from 2‐Alkynylanilines and 2‐Alkynylbenzaldoximes

Recent Advances in Organocatalyst‐Mediated Benzannulation Reactions

Palladium‐Catalyzed Double Cyclization Processes Leading to Polycyclic Heterocycles: Recent Advances

Contact Info

Product

Resources

About