Nickel‐Catalyzed Chemo‐, Regio‐ and Diastereoselective Bond Formation through Proximal CC Cleavage of Benzocyclobutenones

As equential synthesis of b-naphthols and naphtho [2,3-b]furan-2(3H)-ones (naphthofuranones) has been developed using ortho-alkynylarylketonesa st he substrates. The AgTFA-catalyzed ketonization generated the corresponding 1,5-diketonei ntermediates in situ;t hese weref urther cyclized via aldol condensation under basic conditions to obtain b-naphthol products in moderate to good yields. For the synthesis of naphtho[2,3-b]furan-2(3H)-ones, an additional lactonization step was appliedt og ive ab road range of products in good yields. Moreover,t his methodh as also been utilized in the synthesis of natural product negundin A.Scheme1.The reported methodsf or the synthesis of b-naphthols. Scheme2.Our methodology for the synthesis of5min KOH (10.0 equiv), MeOH, 85 8C, 3min < 59 [c] 585 8C, 5min LiOH (10.0equiv), MeOH, 85 8C, 1h < 58 [c] 685 8C, 5min KO t Bu (10.0 equiv), MeOH, rt, 1h < 34 [c] 785 8C, 5min KO t Bu (10.0 equiv), t-BuOH, rt, 1h < 42 [c] 885 8C, 5min KO t Bu (10.0 equiv), THF,rt, 1h -[d] 985 8C, 5min NaO t Bu (10.0 equiv), MeOH, rt, 1h < 51 [c] 10 H 2 O( 1.0 equiv), rt, 15 min KOH (10.0 equiv), MeOH,8 58C, 3min 61 11 H 2 O( 1.0 equiv), rt, 15 min KOH (10.0 equiv), MeOH,r t, 25 min 62 [a] Yields of isolated products are reported. [b] Only 1,5-diketone was observed.[ c] Product containedi mpurities. [d] Complex mixture. [e] O/N = overnight. Scheme3.Substrate scope.Y ields of isolated products are reported. [a] Only the 1,5-diketone was observed;[b] the reaction in step 1w as carried out at 85 8C. Scheme4.Substrate scope expansion. Yields of isolatedproducts are reported. [a] The reaction in step 1w as stirred at room temperature overnight; [b] the reaction in step 1 [b] was stirreda troomtemperaturef or 6h. Scheme5.Reactionmonitoring of compound 1z-OH. Scheme6.Scope of substrate for the synthesis of naphtho[2,3-b]furan-2(3H)ones. Yields of isolated products are reported.[a] The reaction in step 1was carried out at 85 8C. Scheme7.To tal synthesis of negundin A. 1 HNMR (400 MHz, CDCl 3 ): d = 7.66 (d, 1H, J = 8.4 Hz), 7.38-7.32 (m, 2H), 7.26-7.22 (m, 2H), 7.17-7.14 (m, 2H), 7.07-7.05 (m, 2H), 5.06

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Synthesis of β‐Naphthols and Naphthofuranones from ortho‐Alkynylarylketones via Sequential AgTFA‐Catalyzed Ketonization–Intramolecular Aldol Condensation: A Total Synthesis of Negundin A

Nimnual

Norseeda

Akkachairin

et al. 2018

Asian J Org Chem

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Preise 2015 der Real Sociedad Española de Química

2015

Angewandte Chemie

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Synthesis of Multiply Substituted Polycyclic Aromatic Hydrocarbons by Iridium‐Catalyzed Annulation of Ring‐Fused Benzocyclobutenol with Alkyne through C−C Bond Cleavage

Yan

Zhu

2015

Angewandte Chemie

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Nickel‐Catalyzed Chemo‐, Regio‐ and Diastereoselective Bond Formation through Proximal CC Cleavage of Benzocyclobutenones

Cited by 21 publications

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Synthesis of β‐Naphthols and Naphthofuranones from ortho‐Alkynylarylketones via Sequential AgTFA‐Catalyzed Ketonization–Intramolecular Aldol Condensation: A Total Synthesis of Negundin A

Synthesis of β‐Naphthols and Naphthofuranones from ortho‐Alkynylarylketones via Sequential AgTFA‐Catalyzed Ketonization–Intramolecular Aldol Condensation: A Total Synthesis of Negundin A

Preise 2015 der Real Sociedad Española de Química

Synthesis of Multiply Substituted Polycyclic Aromatic Hydrocarbons by Iridium‐Catalyzed Annulation of Ring‐Fused Benzocyclobutenol with Alkyne through C−C Bond Cleavage

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