Synthesis of Atropisomeric 1,8-Bis(4′,4′-dipyridyl)naphthalenes from 4-Trimethylstannylpyridines

Abstract

Two synthetic strategies towards atropisomeric 2′,2′-di­substituted 1,8-bis(4′,4′-dipyridyl)naphthalenes using Stille cross-coupling of trimethylstannylpyridine derivatives and 1,8-di­iodonaphthalene have been investigated. Introduction of substituents into the pyridyl moieties prior to the cross-coupling step provides higher overall yields than derivatization of 1,8-bis(4′,4′-dipyridyl)naphthalene under Ziegler reaction conditions.

Stille coupling - 1,8-dipyridylnaphthalenes - 2,4-disubstituted pyridines - Ziegler reaction - atropisomers

References and Notes

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<A NAME="RM06501SS-11">11</A>

Isolated by flash chromatography (EtOAc-hexanes-Et₃N, 200:200:1). The yield is based on 7. ¹H NMR: δ = 7.47-7.58 (m, 8 H), 8.00 (d, J = 1.5 Hz, 2 H), 8.07 (dd, J = 1.5, 5.1 Hz, 4 H), 8.84 (d, J = 5.1 Hz, 2 H). EI-MS (70 eV): m/z (%) = 308 (100, M⁺), 280 (12, M⁺ - CH₂N), 231 (11, M⁺ - Ph), 204 (24, M⁺ - Ph, - HCN), 176 (13, M⁺ - Ph, - HCN, - CH₂N), 154 (31, M⁺ - 2Ph).