Study On Base-promoted Direct C3-Alkoxymethylation Of Indole

C-H functionalization has attracted considerable attention in the last decade due to it high efficiency, atomic economy, simple operation and easily available starting materials. The regioselectivity remains one of the major challenges in this field since there is always more than one C-H bond in most organic molecules. A variety of directing groups (DGs) have been intensively developed to achieve the desired regioselective control. Heteroaromatic compounds easily realize regioselective C-H activation since heteroatom could make C-H bonds of heteroaromatic ring different reactivity, which has already been applied in the functionalization of various heterocycles. On the other hand, indoles are widely found in bioactive molecules and natural products, and are important intermediates in organic synthesis.In this thesis, we have mainly studied on the synthesis of 3-alkoxyalkylindoles from parent indoles in a one-pot manner via base-promoted multi-molecular cascade reaction (Scheme 1). This protocol features high efficiency, low cost, easy available starting materials, and avoiding transition metal and other additives.According to the results from the controlled experiments and literatures, a plausible reaction mechanism was proposed as follows (Scheme 2):...