Catalytic Benzannulation Reactions of Enynones for Accessing Heterocycle-Incorporating Diarylmethanes

Jia-Yin Wang; Guigen Li; Wen-Juan Hao; Bo Jiang

doi:10.1055/a-1971-6187

Synlett, Inhaltsverzeichnis

Synlett 2023; 34(03): 243-248
DOI: 10.1055/a-1971-6187

letter

Catalytic Benzannulation Reactions of Enynones for Accessing Heterocycle-Incorporating Diarylmethanes

Jia-Yin Wang

^aSchool of Pharmacy, Changzhou University, Changzhou 213164, P. R. of China

^bInstitute of Chemistry and Biomedical Sciences, School of Chemistry and Chemical Engineering, Nanjing University, Nanjing 210093, P. R. of China

,

Guigen Li∗

^bInstitute of Chemistry and Biomedical Sciences, School of Chemistry and Chemical Engineering, Nanjing University, Nanjing 210093, P. R. of China

^cDepartment of Chemistry and Biochemistry, Texas Tech University, Lubbock, Texas 79409, USA

,

Wen-Juan Hao

^dSchool of Chemistry and Materials Science, Jiangsu Key Laboratory of Green Synthetic Chemistry for Functional Materials, Jiangsu Normal University, Xuzhou 221116, P. R. of China

,

Bo Jiang∗

^dSchool of Chemistry and Materials Science, Jiangsu Key Laboratory of Green Synthetic Chemistry for Functional Materials, Jiangsu Normal University, Xuzhou 221116, P. R. of China

› Institutsangaben

Abstract

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Abstract

Two catalytic benzannulation/1,4-addition cascades of available enynones with indoles or tetronic acid-derived enamino lactones as C-nucleophiles are reported, producing 53 examples of heterocycle-incorporating diarylmethanes with moderate to excellent yields. The combination of AgOTf and Sc(OTf)₃ permits bimetallic synergistic catalysis of the reaction of enynones with indoles to access 35 triarylmethanes in generally good yields with ortho-naphthoquinone methides, generated in situ, as the key intermediates. Exchanging indoles for tetronic acid-derived enamino lactones resulted in 18 diarylmethanes by the Ag-catalyzed benzannulation/1,4-addition cascade. Both reactions are advantageous for their high atom utilization and mild reaction conditions, providing intriguing complementary approaches for the direct syntheses of new heterocycle-containing diarylmethanes.

Key words

triarylmethanes - diarylmethanes - benzannulation - 1,4-addition - cascade reaction - enamino lactones

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References and Notes

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14a 4-Methyl-2-[(1-methyl-1H-indol-3-yl)(phenyl)methyl]-1-naphthol (3a); Typical Procedure In a 10 mL reaction vial, enynone 1a (0.4 mmol, 98.4 mg), indole 2a (0.4 mmol, 52.4 mg), AgOTf (0.04 mmol, 10 mol%, 10.2 mg), and Sc(OTf)₃ (0.08 mmol, 20 mol%, 39.4 mg) were mixed in THF (4.0 mL). The mixture was stirred at rt under air for 5 h until the starting material was consumed [TLC, PE–EtOAc (10:1)]. Then the solvent was evaporated under reduced pressure, and the crude product was purified by column chromatography [silica gel, PE–EtOAc (30:1)] to give a white solid; yield: 129.7 mg (86%); mp 174–175 °C. ¹H NMR (400 MHz, CDCl₃): δ = 8.23–8.17 (m, 1 H), 7.95 (d, J = 7.6 Hz, 1 H), 7.57–7.48 (m, 2 H), 7.39–7.30 (m, 7 H), 7.28–7.24 (m, 1 H), 7.09–7.01 (m, 2 H), 6.60 (s, 1 H), 5.90 (s, 1 H), 5.70 (s, 1 H), 3.74 (s, 3 H), 2.59 (s, 3 H). ¹³C NMR (100 MHz, CDCl₃): δ = 148.1, 142.2, 137.8, 132.6, 129.0, 128.7, 128.7, 128.6, 127.3, 126.8, 126.1, 125.7, 125.5, 124.8, 124.0, 122.4, 122.3, 121.9, 119.9, 119.4, 115.6, 109.4, 45.0, 32.9, 18.9. HRMS (ESI): m/z [M + H]⁺ calcd for C₂₇H₂₄NO: 378.1858; found: 378.1855.
14b 3-[(1-Hydroxy-4-methyl-2-naphthyl)(phenyl)methyl]-4-[(4-methylphenyl)amino]furan-2(5H)-one; Typical Procedure In a 10 mL reaction vial, enynone 1a (0.3 mmol, 73.8 mg), 4-(p-tolylamino)furan-2(5H)-one (4a, 0.3 mmol, 56.7 mg), and AgOTf (0.03 mmol, 10 mol%, 7.7 mg) were mixed in 1,4-dioxane (4.0 mL). The mixture was then stirred at 50 °C under air for 2 h until the starting material was consumed [TLC, PE–EtOAc (2:1)]. The solvent was then evaporated under reduced pressure, and the crude product was purified by column chromatography [silica gel, PE–EtOAc (6:1)] to give a white solid; yield: 117.5 mg (90%); mp 159–161 °C. ¹H NMR (400 MHz, CDCl₃): δ = 8.38–8.22 (m, 1 H), 8.01–7.89 (m, 1 H), 7.58–7.51 (m, 2 H), 7.43–7.33 (m, 5 H), 7.12 (d, J = 8.8 Hz, 3 H), 6.87 (d, J = 6.4 Hz, 1 H), 6.79 (s, 1 H), 6.71 (d, J = 8.4 Hz, 2 H), 5.73 (s, 1 H), 4.89–4.79 (m, 2 H), 2.61 (s, 3 H), 2.32 (s, 3 H). ¹³C NMR (100 MHz, CDCl₃): δ = 176.4, 160.6, 147.9, 138.3, 135.7, 135.6, 132.7, 130.3, 129.1, 128.2, 127.6, 127.3, 127.2, 126.6, 126.1, 125.4, 124.0, 122.8, 121.8, 121.1, 98.3, 66.8, 40.5, 20.8, 19.0. HRMS (ESI): m/z [M + H]⁺ calcd for C₂₉H₂₆NO₃: 436.1913; found: 436.1879.

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