Catalytic Functionalization of C(sp2)H and C(sp3)H Bonds by Using Bidentate Directing Groups. Issue 45 (17th September 2013) - Rouquet, Guy
Abstract CH bonds are ubiquitous in organic compounds. It would, therefore, appear that direct functionalization of substrates by activation of CH bonds would eliminate the multiple steps and limitations associated with the preparation of functionalized starting materials. Regioselectivity is an important issue because organic molecules can contain a wide variety of CH bonds. The use of a directing group can largely overcome the issue of regiocontrol by allowing the catalyst to come into proximity with the targeted CH bonds. A wide variety of functional groups have been evaluated for use as directing groups in the transformation of CH bonds. In 2005, Daugulis reported the arylation of unactivated C(sp3)H bonds by using 8‐aminoquinoline and picolinamide as bidentate directing groups, with Pd(OAc)2 as the catalyst. Encouraged by these promising results, a number of transformations of CH bonds have since been developed by using systems based on bidentate directing groups. In this Review, recent advances in this area are discussed.