Palladium‐Catalyzed Carbonylation Reaction of Indole/Pyrrole Involving HCFO‐1233zd (E)

Abstract

3‐Idolenone is a key intermediate in the synthesis of many drugs and plays an important role in synthetic chemistry and biochemistry. A new method for the synthesis of trifluoromethylated 3‐indolenones by carbonylation catalyzed by Pd(0) is described. In the absence of an additive, 1‐chloro‐3,3,3‐trifluoro‐propylene (an inexpensive ozone‐friendly CF3 structural unit) reacts with indole and carbon monoxide to synthesize trifluoromethylatedindolenone in good yield, regioselectivity and chemoselectivity and with strong resistance to basal functional groups such as alkynes, aldehydes and esters. Notably, in addition to indole compounds being well transformed into the corresponding products, pyrrole, heteroindole can also is also suitable for the corresponding chemical transformation. This study provides a scientific method for the late construction of trifluoromethylated indole/pyrrole 3‐ketene.