One‐Pot Synthesis of Polysubstituted Benzenes through a <i>N</i>,<i>N</i>‐dimethyl‐4‐aminopyridine (DMAP)‐Catalyzed [4+2] Benzannulation of 1,3‐Bis(sulfonyl)butadienes and γ‐Substituted Allenoates

Chang, Meijia; Wu, Congcong; Zheng, Jie; Huang, You

doi:10.1002/asia.201600102

Cited by 31 publications

(9 citation statements)

References 94 publications

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“…For example, in 2016, Huang's group disclosed an efficient method to attain polysubstituted benzenes 84 via the annulation of dienic sulfones 82 and a-substituted allenoates 83 (Scheme 24). 44 The reaction proceeded successfully with DMAP as the catalyst and CH 3 COONa as the additive in CHCl 3 at 60 C. Various substituents on 82 or 83 were well tolerated, providing product 84 in acceptable-to-good yields (29-72%) with high regioselectivity. However, low yields were observed when the benzene core beard an electron-decient (NO 2 ) or an electron-rich group (OMe).…”

Section: [4 + 2] Benzannulationmentioning

confidence: 96%

Synthesis of polysubstituted arenes through organocatalytic benzannulation

et al. 2020

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Section: [4 + 2] Benzannulationmentioning

confidence: 96%

Synthesis of polysubstituted arenes through organocatalytic benzannulation

et al. 2020

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“…In 2016, Huang and co-workers reported a DMAP-catalyzed (4 + 2) benzannulation from readily prepared 1,3-bis(sulfonyl) butadienes 11 and γ-substituted allenoates 12. [32] When only DMAP was used as catalyst, the multi-substituted cyclohexene 46 a and cyclohexadiene derivative 47 a were obtained in moderate yields. It was found that the additives including inorganic bases (e. g., CH 3 CO 2 Na, NaOH, Cs 2 CO 3 ), organic bases (e. g., NEt 3 , DIPEA) as well as Brønsted acid (PhCOOH) could switch the selectivity of the benzannulation reaction to generate the polysubstituted benzenes 48 (Scheme 9).…”

Section: Tertiary Amine-mediated Benzannulation Reactionsmentioning

confidence: 99%

Recent Advances in Organocatalyst‐Mediated Benzannulation Reactions

2020

Adv Synth Catal

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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.

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“…Recently, Huang and co‐workers demonstrated a DMAP‐catalyzed [4+2] benzannulation reaction of 1,3‐bis(sulfonyl)butadienes 136 with γ‐substituted allenoates 137 for the regioselective synthesis of polysubstituted benzenes 138 by using 30 mol % CH 3 COONa as an additive (Scheme ) . Dienic sulfones that contained a moderately electron‐donating group (CH 3 ) or an electron‐withdrawing group (Br, Cl, F, or CF 3 ) on the benzene ring afforded the corresponding benzannulated derivatives in moderate‐to‐good yields.…”

Section: Dmap‐mediated Benzannulation Reactionsmentioning

confidence: 99%

Recent Progress in Transition‐Metal‐Free, Base‐Mediated Benzannulation Reactions for the Synthesis of a Diverse Range of Aromatic and Heteroaromatic Compounds

et al. 2018

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Benzene and itsderivativesare the most abundant substructures of several interesting classes of compound, such as bioactive molecules. Owing to their importance, the development of methods for their constructionh as attracted considerable attention.H owever,t he regioselectives ynthesis of polysubstituted aromatic and heteroaromatic compounds by using aromatic substitution is challenging, because it provides derivatives with restricted substitution patterns. Therefore, the benzannulation reaction-the assembly of benzene derivatives from acyclicp recursors-constitutes as uperior and highly versatile approach to polysubstituted aromatic and heteroaromatic compounds,a nd variouse fficient benzannulation reactions have been reported.R epresentative examples include Cs 2 CO 3 , t-BuOK,a nd DBU-catalyzed reactions for the construction of valuableb enzene derivatives. The central objective of this Focus Review is to highlight base-mediated benzannulation reactions under transitionmetal-free conditions for the construction of aromatic and heteroaromatic compounds.[a] Dr.Recently,P an and co-workers investigated the K 2 CO 3 -catalyzed cascade benzannulation reaction of b-keto sulfones 1 with acetylene ketones 2 by using 30 %m ol K 2 CO 3 without other additives,w hich afforded new sulfonylbenzene derivatives 3 in good yields through ab enzannulation reaction (Scheme 1a). [18] Av ariety of electron-donating ande lectron-withdrawing groups were well-tolerated under the optimized reaction conditions. The proposed reactionpathway proceeded through se-quentialM ichael addition, intramolecular cyclization, hydrogen abstraction, and dehydration reactions (Scheme 1b).Scheme55. Synthesis of unsymmetrical biaryls from the annulation/aromatizationr eactionsof1 ,4-pentanedienes with nitroalkanes.Scheme56. DBU-promoted [5+ +1] annulation reaction of a-alkenoyl ketene-S,S-acetalswith nitroalkanes.

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One‐Pot Synthesis of Polysubstituted Benzenes through a N,N‐dimethyl‐4‐aminopyridine (DMAP)‐Catalyzed [4+2] Benzannulation of 1,3‐Bis(sulfonyl)butadienes and γ‐Substituted Allenoates

Cited by 31 publications

References 94 publications

Synthesis of polysubstituted arenes through organocatalytic benzannulation

Synthesis of polysubstituted arenes through organocatalytic benzannulation

Recent Advances in Organocatalyst‐Mediated Benzannulation Reactions

Recent Progress in Transition‐Metal‐Free, Base‐Mediated Benzannulation Reactions for the Synthesis of a Diverse Range of Aromatic and Heteroaromatic Compounds

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