Jean‐Michel Becht1,2, Arnaud Gissot3,2, Alain Wagner2, Charles Mioskowski2
1IS2M - Institut de Science des Matériaux de Mulhouse (15 rue Jean Starcky BP 2488 68057 MULHOUSE CEDEX 2 - France)
2Laboratoire de Synthèse Bioorganique (74 route du Rhin 67401 Illkirch-Graffen-staden - France)
3ARNA - Acides Nucléiques : Régulations Naturelle et Artificielle (IECB - 2 rue Robert Escarpit 33607 Pessac. - France)
Tóm tắt
AbstractNoncatalyzed coupling reactions of aryllithiums and haloarenes proceed not only through the well‐known aryne route but also, in some cases, through a novel addition–elimination pathway. Indeed, ortho‐chloro‐ and ortho‐bromomethoxyarenes lead selectively to the corresponding ortho‐biaryls through a chelation‐driven aromatic nucleophilic substitution pathway. Contrary to common belief, such noncatalyzed coupling reactions often proceed with high regioselectivity and high yield. These results underline the potency of such simple reactions and open up a straightforward access to a wide range of biaryl structures; this also appears particularly useful for large‐scale and biaryl building‐block syntheses, as only cheap and readily available substrates are involved.
