Dirhodium tetraacetate: An effective catalyst in organic synthesis

Abstract

(A) Rh(II)-catalyzed regioselective intramolecular and regiospecific intermolecular CH insertion into aliphatic and aromatic C-H bonds is a very powerful methodology for the synthesis of a diverse range of organic compounds. (B) Rh2(OAc)4 is a very useful catalyst for two-component-cycloaddition as well as three-component 1,3-dipolar cycloaddition reactions. (C) On treatment with catalytic rhodium(II) acetate, cyclic diazoamides and diazoamines furnished the corresponding cyclic enamides and Z enamines, repectively. (D) Allylic and benzylic alcohols were oxidized to the corresponding carbonyl compounds using tert-butyl hydroperoxide in stoichiometric amounts and Rh2(OAc)4 as catalyst (1 mol%) in dichloromethane at ambient temperature. (E) Intramolecular 1,2-insertions into C-C bonds by Rh(II) carbenoids have been used for the synthesis of substituted dienes. (F) Rh(II) carbenoids react with amines, alcohols or thiols to yield the product of a formal intra- or intermolecular X-H bond (X = N/O/S) insertion via the formation of an ylide intermediate. (G) Rh(II) carbenoids react readily with lone pairs giving the corresponding ylides, which are valuable intermediates, capable of undergoing a broad range of synthetically useful transformations. (H) Rh2(OAc)4 is an effective catalyst for the intra- and intermolecular cyclopropanation reactions through the decomposition of diazocarbonyl compounds. (I) Du Bois et al. reported the Rh(II)-catalyzed oxidative cyclization of sulfamate and carbamate esters. © Georg Thieme Verlag Stuttgart.