Synthesis and reactivity of 2-thionoester pyrroles: a route to 2-formyl pyrroles
Kim, Min Joon
Gaube, Sophie M.
Beh, Michael H. R.
Smith, Craig D.
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2-Functionalised pyrroles exhibit considerable synthetic utility. Herein, the synthesis and reactivity of 2-thionoester (-C(S)OR) pyrroles is reported. 2-Thionoester pyrroles were synthesized using a Knorr-type approach from aliphatic starting materials. 2-Thionoester pyrroles were reduced to the corresponding 2-formyl pyrroles, or the deuterated formyl variant, in one step using Raney nickel, thereby removing the need for the much-utilized hydrolysis/decarboxylation/formylation steps that are typically required to convert Knorr-type 2-carboxylate pyrroles into 2-formyl pyrroles. 2-Thionoester pyrroles proved tolerant of typical functional group interconversions for which the parent 2-carboxylate pyrroles have become known.
Kim, Min Joon; Gaube, Sophie M.; Beh, Michael H. R.; Smith, Craig D.; Thompson, Alison. (2019). RSC Advances.