Abstract
Rhodium-catalyzed synthesis of 2,3-disubstituted indoles from β,β-disubstituted stryryl azides.
Highlights
The effect of transition metal complexes on the desired migration was investigated using a mixture of the E- and Zisomer of b,b-disubstituted aryl azide 8 (Table 1)
Catalyst. [e] 10 % aryl azide remained. [f ] No molecular sieve added. Indicate whether this process can be rendered selective for styryl azides 4 that contain two different b-substituents to form 2,3-disubstituted indoles
Examination of a range of dirhodium(II) complexes revealed that selective formation of 9 was obtained using with [Rh2(O2CC3F7)4],[8,13] [Rh2(O2CC7H15)4], or [Rh2(esp)2][14] (Table 1, entries 1–7).[15]
Summary
Rhodium-Catalyzed Synthesis of 2,3-Disubstituted Indoles from b,b-Disubstituted Stryryl Azides**. Controlling the selectivity of the migration step is critical to the success of these transformations.[1] Sequential reaction processes that involve metal nitrenes are rare despite their electrophilicity,[2] which enables reaction with carbon– hydrogen bonds or olefins.[3,4,5,6] Our mechanistic study of rhodium(II)-catalyzed carbazole formation from biaryl azides which suggested that CÀN bond formation preceded CÀH bond cleavage through a 4p-electron–5-atom electrocyclization.[7] we anticipated that substrates lacking functionalizable CÀH bonds might participate in a migratorial process where a new CÀC bond is formed in addition to the CÀN bond.
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