Silver and Brønsted Acid Catalyzed Nazarov‐Type Cyclizations To Generate Benzofulvenes

Cordier, Pierre; Aubert, Corinne; Malacrìa, Max; Lacôte, Emmanuel; Gandon, Vincent

doi:10.1002/anie.200903675

Cited by 103 publications

(39 citation statements)

References 41 publications

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“…[24] Similar treatment of the products of twofold cross-coupling led to aclean and completely regioselective 4 p electrocyclization/Friedel-Crafts cyclization to form highly substituted indenes (Scheme 3b). [24] Similar treatment of the products of twofold cross-coupling led to aclean and completely regioselective 4 p electrocyclization/Friedel-Crafts cyclization to form highly substituted indenes (Scheme 3b).…”

Section: Methodsmentioning

confidence: 99%

Direct Cross‐Couplings of Propargylic Diols

2016

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Pd(PPh 3 ) 4 ]c atalyzes aS uzuki-Miyaura-like twofold cross-coupling sequence between underivatized propargylic diols and either aryl or alkenyl boronic acids to furnish highly substituted 1,3-dienes.T hus,2 ,3-diaryl-1,3-butadienes and their dialkenic congeners ([4]dendralenes) are delivered in a(pseudo)halogen-free,single-step synthesis which supersedes existing methods.A llenols are also readily formed. Treatment of these single-and twofold cross-coupled products with acid leads to remarkably short syntheses of highly-substituted benzofulvenes and aryl indenes,r espectively.

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Section: Methodsmentioning

confidence: 99%

Direct Cross‐Couplings of Propargylic Diols

2016

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“…This latter step proposed has been described to be catalyzed by Brønsted or Lewis acids from -allenyl benzyl alcohols. [16] Scheme 3. Detailed mechanism based on our computational exploration.…”

Section: Methodsmentioning

confidence: 99%

Brønsted Acid‐Catalyzed Cascade Reactions Involving 1,2‐Indole Migration

Álvarez

Faza

López

et al. 2015

Chemistry A European J

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A cascade reaction of indoles with propargylic diols involving an unprecedented metal-free 1,2-indole migration onto an alkyne is here described. DFT calculations support a mechanism consisting in a concerted nucleophilic attack of the indole nucleus with loss of water followed by the 1,2-migration and subsequent Nazarov cyclization. This Brønsted acid-catalyzed protocol affords indole-functionalized benzofulvene derivatives in high yields.

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“…No clear reactivity trend could be deduced from these results. Boc-protection of MBH alcohols with Boc 2 O and DMAP gave moderate to high yields for γ-MBH products 4 (entries 13-16) and low to moderate yields for α-MBH products 5 (entries [17][18][19][20]. Again, reactivity differences between diastereomeric substrates were clear, but followed no apparent trend.…”

Section: Letter Syn Lettmentioning

confidence: 96%

Diastereomerically Pure Morita–Baylis–Hillman (MBH) Acetates and Carbonates from Allenic α- and γ-MBH Alcohols

Selig

Nghiem

2015

Synlett

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Me CO 2 Et Me O Ar CO 2 Et Ar O t-Bu X X * * * * X = H X = Ac X = Boc MBH alcohols MBH acetates MBH carbonates • α-and γ-MBH derivatives • separate diastereoisomers Abstract Diastereomerically pure allenic Morita-Baylis-Hillman (MBH) acetates and carbonates have been prepared from their corresponding α-and γ-MBH alcohols. Derivatizations proceeded under standard conditions without epimerization. Both α-and γ-MBH derivatives were shown to be suitable substrates for further transformations.

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Silver and Brønsted Acid Catalyzed Nazarov‐Type Cyclizations To Generate Benzofulvenes

Cited by 103 publications

References 41 publications

Direct Cross‐Couplings of Propargylic Diols

Direct Cross‐Couplings of Propargylic Diols

Brønsted Acid‐Catalyzed Cascade Reactions Involving 1,2‐Indole Migration

Diastereomerically Pure Morita–Baylis–Hillman (MBH) Acetates and Carbonates from Allenic α- and γ-MBH Alcohols

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