Oxidative Biaryl Coupling of N-Aryl Anilines by Using a Hypervalent Iodine(III) Reagent

Dedicated to Victor Snieckus in honor of his 80^th birthday

Abstract

Biaryl diamines are important building blocks in organic ­synthesis. Consequently, it is desirable to develop a general and mild synthetic approach to diverse biaryl diamines. Oxidative coupling is an efficient and promising strategy for the synthesis of these targets. We have now developed a direct formation of biaryl diamines by oxidative coupling using a hypervalent iodine(III) reagent.

Key words

biaryl diamines - hypervalent iodine - oxidative coupling

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• 20 Oxidative Coupling of N-Arylnaphthalenamines 1; General Procedure PIFA (0.75 equiv.) was added to a stirred solution of the appropriate naphthalenamine 1 (0.30 mmol, 1 equiv) in DCE (3 mL) at r.t., and the mixture was stirred for 30 min. When the reaction was complete, sat. aq NaHCO₃ was added to the mixture, and the aqueous phase was extracted with CH₂Cl₂. The extracts were dried (Na₂SO₄) and evaporated to dryness, and the crude residue was purified by column chromatography (silica gel, hexane–EtOAc). N,N′-Diphenyl-(1,1′-binaphthyl)-4,4′-diamine (2a) ^{8c 1}H NMR (400 MHz, CDCl₃): δ = 6.04 (s, 2 H), 6.95 (t, J = 7.6 Hz, 2 H), 7.11 (dd, J = 1.2, 8.8 Hz, 4 H), 7.29–7.35 (m, 6 H), 7.41 (d, J = 7.6 Hz, 2 H), 7.46–7.51 (m, 6 H), 8.14 (d, J = 8.4 Hz, 2 H). ¹³C NMR (100 MHz, CDCl₃): δ = 115.1, 117.6, 120.6, 121.8, 125.5, 126.1, 127.4, 127.5, 128.3, 129.4, 133.3, 134.1, 138.5, 144.6. N,N′-bis(4-Tolyl)-1,1′-binaphthalene-4,4′-diamine (2b) ^{8c 1}H NMR (400 MHz, CDCl₃): δ = 2.33 (s, 6 H), 6.00 (s, 2 H), 7.05 (d, J = 8.4 Hz, 4 H), 7.13 (d, J = 8.4 Hz, 4 H), 7.30 (t, J = 7.6 Hz, 2 H), 7.36–7.37 (m, 4 H), 7.44–7.50 (m, 4 H), 8.11 (d, J = 8.8 Hz, 2 H). ¹³C NMR (100 MHz, CDCl₃): δ = 20.7, 113.4, 118.7, 121.5, 125.4, 126.0, 126.9, 127.4, 128.3, 129.9, 130.6, 132.5, 134.1, 139.3, 141.6. N,N′-Bis(4-bromophenyl)-N,N′-diphenyl-1,1′-binaphthalene-4,4′-diamine (2e) IR (KBr): 3064, 3037, 1582, 1485, 1272, 910, 736 cm^–1. ¹H NMR (CDCl₃): δ = 6.97 (d, J = 8.8 Hz, 4 H), 7.02 (t, J = 7.2 Hz, 2 H), 7.15 (d, J = 7.6 Hz, 4 H), 7.26–7.34 (m, 10 H), 7.38 (t, J = 6.8 Hz, 2 H), 7.42 (d, J = 7.6 Hz, 2 H), 7.49 (d, J = 8.0 Hz, 2 H), 7.51 (d, J = 7.6 Hz, 2 H), 8.02 (d, J = 8.0 Hz, 2 H). ¹³C NMR (CDCl₃): δ = 113.8, 122.50, 122.53, 123.0, 124.3, 126.4, 126.5, 126.6, 127.2, 128.5, 129.3, 131.0, 132.1, 134.5, 136.8, 142.9, 147.7, 147.9. MS (MALDI-TOF): m/z = 744.12 [M⁺]. N,N,N′,N′-Tetraphenyl-1,1′-binaphthalene-2,2′-diamine (2g) ^{19 1}H NMR (CDCl₃): δ = 6.44 (d, J = 8.1 Hz, 2 H), 6.45–6.58 (m, 12 H), 6.61–6.77 (m, 10 H), 7.12 (td, J = 1.2, 7.6 Hz, 2 H), 7.62 (m, 4 H), 7.78 (d, J = 8.6 Hz, 2 H). ¹³C NMR (CDCl₃): δ = 121.7, 123.2, 124.4, 125.2, 126.6, 126.7, 127.1, 128.3, 128.7, 131.2, 131.7, 134.0, 144.4, 147.2. Catalytic Oxidative Coupling of N-Phenylnaphthalen-1-amine (1a) PhI (10 mol%) and TFA (0.2 equiv) were added to a stirred solution of amine 1a (1 equiv) in 1:1 DCE/HFIP (0.67 M) at r.t. mCPBA (0.75 equiv) was then gradually added, and the mixture was stirred for 3 h under at r.t. When the reaction was complete (TLC), sat. aq NaHCO₃ was added to the mixture, and the aqueous phase was extracted with CH₂Cl₂. The extracts were dried (Na₂SO₄) and then evaporated to dryness. The crude residue was purified by column chromatography (silica gel, hexane/EtOAc) to give pure 2a; yield: 71%.