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Short Paper | Regular issue | Vol 87, No. 10, 2013, pp.2109-2118
Published online, 23rd August, 2013
DOI: 10.3987/COM-13-12804
C–H MODIFICATION OF 2-AZAADAMANTANE: SYNTHESIS OF C5-FUNCTIONALIZED AZADOS FOR ADVANCED USE

Yusuke Sasano, Tomohiro Nishiyama, Masaki Tomizawa, Masatoshi Shibuya, and Yoshiharu Iwabuchi*

*Graduate School of Pharmaceutical Sciences, Tohoku University, 6-3 Aobayama, Sendai 980-8578, Japan

Abstract

Regioselective C–H functionalization of N-protected 2-azaadamantane was achieved via a radical-induced bromination. The obtained 5-bromo-2-azaadamantane is readily transformed to arylated/alkylated 2-azaadamantane N-oxyls [AZADOs], which exhibit high catalytic activities for alcohol oxidation.