Divergent Copper‐salt‐controlled Reactions of Donor‐Acceptor Cyclopropanes and <i>N</i>‐Fluorobenzene Sulfonimide: Access to the 1,3‐Haloamines and Aminoindanes
Lingyan Liu, Xiao Wang, Weiguo Xiao, Weixing Chang, Jing Li
Abstract
Abstract We herein report a method for divergent copper salt controlled reactions of donor‐acceptor cyclopropanes and N ‐fluorobenzene sulfonimide (NFSI). Specifically, in the presence of CuX 2 (X=Cl, Br), the cyclopropanes underwent formal umpolung 1,3‐aminohalogenation bifunctionalization via a free radical mediated ring‐opening process to afford 1,3‐aminochlorination and 1,3‐aminobromination products in moderate to good yields. In addition, by using CuI as a catalyst, we synthesized various aminoindane derivatives via 1,3‐aminoarylation cyclization of D‐A cyclopropanes, the reactions involved a free radical mediated ring‐opening and subsequent ring expansion via C−H bond activation.