Abstract
AbstractA theoretical study of the role of added salts, solvent effects, and substrate scope for the RhIII‐catalyzed C–H activation and annulation of N‐(pivaloyloxy)benzamide and alkyne MIDA boronates has been performed by means of DFT calculations. Computationally, the high reactivity of terminal alkynyl MIDA boronates originates from the electronic stability of the sp3‐hybridized boronate. The critical role of Cu(OAc)2 as additive is such that it can be viewed as an intermediate catalyst, assisting the removal of the directing group and facilitating the conversion of RhI into RhIII in the intramolecular oxidative addition process. In contrast, AgOAc seems to have an opposite effect because it increases the activation free‐energy barrier for the migratory insertion step, retarding the chemical transformation and reducing the product yield. Solvent selectivity, regioselectivity and substituent effects have also been investigated.
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