Palladium-catalyzed carbonylation with direct indole C-H activation
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 biochemi-stry. A new
method for the synthesis of trifluoromethylated 3-indolenones by
carbonylation reaction catalyzed by Pd (0) is de-scribed. In the absence
of an additive, 1-chloro-3,3,3-trifluoro-propylene (a cheap
ozone-friendly CF3 structural unit) reacts with indole and carbon
monoxide to synthesize trifluoromethylatedindolenone, good yield,
Regioselectivity and Chemoselectivity, and strong resistance to basal
functional groups such as alkynes, aldehydes and esters. It is worth
mentioning that not only indole compounds can be well transformed into
the corresponding products, pyrrole, hetero-indole also can be well
completed the cor-responding chemical transformation. This late
construction of trifluoromethylated indole/pyrrole 3-ketene provides a
scientific method.