Axially Chiral Phenanthroline Ligand-Enabled Copper-Catalyzed Enantioselective Arylation of Azonaphthalenes with Arylboronic Acids

Abstract

An axially chiral phenanthroline ligand bearing two BINOL units was found to be capable of promoting the copper-catalyzed enantioselective arylation of 2-azonaphthalenes with arylboronic acids. This atroposelective Michael-type addition affords a range of enantioenriched axially chiral biaryl compounds in synthetically useful yields with enantiomeric ratios of up to 91.5:8.5.

Key words

asymmetric catalysis - phenanthroline ligands - copper catalysis - azonaphthalenes - arylboronic acids - biaryls

Publication History

Received: 15 July 2024

Accepted after revision: 15 August 2024

Accepted Manuscript online:
15 August 2024

Article published online:
09 October 2024

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• 14 Copper-Catalyzed Enantioselective Arylation of Azonaphthalenes with Arylboronic Acids; General Procedure A reaction tube (10 mL) equipped with a magnetic stirrer bar was charged with CuCl₂·2H₂O (1.8 mg, 0.01 mmol), ligand L5 (7.6 mg, 0.01 mmol), and CH₂Cl₂ (3 mL), and the mixture was stirred at r.t. for 2 h. The appropriate azonaphthalene 2 (0.1 mmol), arylboronic acid 15 (0.15 mmol), and KHCO₃ (15 mg, 0.15 mmol) were added, and the mixture was stirred at 25 °C for 3 d. The resulting mixture was directly purified by flash chromatography (silica gel, PE–EtOAc). Benzyl (S)-2-(1,1′-Binaphthalen-2-yl)hydrazinecarboxylate (16a) Yellow oil; yield: 27 mg (64%, er 87.5:12.5); [α]_D ²⁰ = +24.2 (c = 0.39, CHCl₃). HPLC [Chiralcel OD-H, hexane–i-PrOH (92:8), 1.0 mL/min, λ = 254 nm]: t_{R (major)} = 23.3 min; t_{R (minor)} = 26.6 min. ¹H NMR (400 MHz, CDCl₃): δ = 7.94 (d, J = 8.0 Hz, 1 H), 7.91 (d, J = 8.4 Hz, 1 H), 7.86 (d, J = 9.2 Hz, 1 H), 7.81 (d, J = 8.4 Hz, 1 H), 7.60–7.55 (m, 2 H), 7.44 (t, J = 7.6 Hz, 1 H), 7.36 (d, J = 8.8 Hz, 2 H), 7.29–6.91 (m, 9 H), 6.56 (br s, 1 H), 5.54 (br s, 1 H), 5.04 (s, 2 H). ¹³C NMR (101 MHz, CDCl₃): δ = 166.11, 156.85, 143.28, 135.75, 134.14, 133.91, 133.30, 132.72, 129.61, 129.43, 129.24, 129.11, 128.68, 128.43, 128.33, 128.04, 126.60, 126.40, 126.24, 126.03, 125.02, 123.34, 118.81, 114.18, 67.57. The absolute configuration of 16a was assigned by reference to the literature.^5f