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Synlett 2021; 32(10): 993-998
DOI: 10.1055/a-1458-5785
DOI: 10.1055/a-1458-5785
letter
Visible-Light Photoredox-Catalyzed Decarboxylative α-tert-Butylation of C(sp3)–H Bonds of N-Aryltetrahydroisoquinolines with Pivalic Acid under Transition-Metal-Free Conditions
We gratefully acknowledge financial support from the National Natural Science Foundation of China (21901081), the Young Talent Key Project of Anhui Province (170808J02), the Natural Science Foundation of Anhui Province (2008085QB90), and the Project of Anhui Provincial Education Department (KJ2015TD002).
Abstract
A transition-metal-free visible-light photoredox-catalyzed decarboxylative alkylation of the benzylic C(sp3)–H bonds of N-aryltetrahydroisoquinolines is reported. The method tolerates various functional groups and proceeds smoothly without requiring a stoichiometric oxidant. A preliminary mechanistic study indicated that a radical process is involved in the reaction.
Key words
photoredox catalysis - decarboxylation - alkylation - tetrahydroisoquinolines - carboxylic acids - organocatalysisSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-1458-5785.
- Supporting Information
Publication History
Received: 21 February 2021
Accepted after revision: 22 March 2021
Accepted Manuscript online:
22 March 2021
Article published online:
12 April 2021
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- 18 1-(tert-Butyl)-2-phenyl-1,2,3,4-tetrahydroisoquinoline (3a); Typical ProcedureA tubular vessel containing a stirrer bar was charged with 1a (0.2 mmol), pivalic acid (2a; 0.5 mmol), [Acr+-Mes]ClO4 (3.0 mol%), Na2HPO4·12 H2O (0.4 mmol), acetone (1.5 mL), and H2O (1.5 mL). The mixture was stirred and irradiated by a blue LED (450–455 nm, 1.5 W) for 12 h in air at rt. When the reaction was complete, the mixture was diluted with H2O and extracted with EtOAc. The organic layers were combined, dried (Na2SO4), filtered, and concentrated. The crude product was purified by flash chromatography [silica gel, PE–EtOAc (20:1 to 9:1)] to give a white solid; yield: 36.09 mg (68%); mp 78.5–79.0 °C.1H NMR (600 MHz, CDCl3): δ = 7.21–7.19 (m, 2 H), 7.15 (s, 2 H), 7.12 (s, 2 H), 6.92 (d, J = 7.8 Hz, 2 H), 6.68–6.66 (m, 1 H), 4.67 (s, 1 H), 3.88–3.86 (m, 1 H), 3.56–3.51 (m, 1 H), 3.07–3.05 (m, 1 H), 3.00–2.97 (m, 1 H), 1.02 (s, 9 H). 13C NMR (150 MHz, CDCl3): δ = 151.2, 137.0, 135.4, 129.0, 128.7, 128.3, 126.5, 125.0, 116.6, 114.2, 66.0, 44.0, 39.2, 29.2, 27.3. HRMS (ESI): m/z [M + H]+ calcd for C19H24N: 266.1903; found: 266.1905.
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