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N-aryl-substituted nitrones were employed as five-atom coupling partners in the rhodium-catalyzed cyclization with diynes. In this reaction, the nitrone moiety served as a directing group for the catalytic CH activation of the N-aryl ring. This formal [2+2+5] approach allows rapid access to bridged eight-membered heterocycles with broad substrate scope. The results of this study may provide new insight into the chemistry of nitrones and find applications in the synthesis of other heterocycles. [ABSTRACT FROM AUTHOR]

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C13H10AgBF4N2O3, orthorhombic, Pbca (no. 61), a = 13.2751(5) Å, b = 14.6212(5) Å, c = 15.5573(6) Å, V = 3019.6 Å3, Z = 8, Rgt(F) = 0.0498, wRref(F2) = 0.1423, T = 296 K. [ABSTRACT FROM AUTHOR]