Benzylic functionalization of (eta(6)-alkylarene)chromium tricarbonyl complexes

A general method for the regioselective benzylic metallation of (eta(6)-alkylarene)chromium tricarbonyl complexes on the action of lithium amides in THF under very mild conditions has been developed. Transmetallation reactions of the lithium derivatives thus obtained produce the corresponding benzylic organotin, zinc and copper chromium tricarbonyl complexes. Methods for the preparative benzylic functionalization of (eta(6)-alkylarene)chromium tricarbonyl complexes have been developed, including carboxylation, alpha-hydroxyalkylation, gamma-carbonylation, acylation, arylation, vinylation, heteroarylation and alkylation procedures. 5-Acetoxy-3-benzyl-1,4-methano-2,3,4,5-tetrahydro-1H-3-benzazepine has been prepared using the benzylic lithium derivative of the (eta(6)-alkylarene)chromium tricarbonyl complex at the key step. This compound is a representative of the major class of physiologically active compounds known as C-norbenzomorphans. (C) 1997 Elsevier Science S.A.