Copper Catalyzed Cleavage Of Esters Under Nearly Neutral Conditions In The Present Of NaN₃

Cleavage of esters to alcohols constitutes a significant position in functional group transformation. Masking of a alcohol group is a frequently desirable transformation in organic synthesis and considering the ease of preparation and the availability of starting materials, alcohol function are often protected as their acyl groups. Thus, the development of a mild and efficient method for the cleavage of esters as a deprotection procedure is a significant aspect of experimental organic chemistry.From the past reptort, despite the fact that many methods already exist for the cleavage of esters, most of them suffer from some drawbacks, such as odoriferous fumes, moisture sensitive and strong basic reaction conditions. So we want to use copper as catalyst developing a new, mild and general approach under atmospheric neutral reaction conditions in moderate to excellent yields.In this paper, we research the reduction of esters using sodium azide in the presence of a catalytic amount of copper carbonate in MeOH was examined. The method provides a complementary means of cleavage of esters under neutral condtions. Under the optimized reaction condition, Cu2(OH)2CO3 was found to process the highest activity and efficiently enhanced deprotection of aryl and alkyl esters with heteroatom or functional grous to give their corresponding alcohols in good yield.According to the results, we found this method is a very simple, mild and highly efficient practical protocol for deprotection of esters. The catalyst is cheap, readily available and neutral. The reaction is environmentally friendly and results in excellent yields of desired products.