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Synlett 2023; 34(03): 243-248
DOI: 10.1055/a-1971-6187
DOI: 10.1055/a-1971-6187
letter
Catalytic Benzannulation Reactions of Enynones for Accessing Heterocycle-Incorporating Diarylmethanes
National Natural Science Foundation of China (No. 21971090, 22071102, and 91956110) and the Robert A. Welch Foundation (D-1361-20210327).
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 lactonesSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-1971-6187.
- Supporting Information
Publication History
Received: 20 September 2022
Accepted after revision: 02 November 2022
Accepted Manuscript online:
02 November 2022
Article published online:
28 November 2022
© 2022. Thieme. All rights reserved
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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.