A transition‐metal‐free, redox‐neutral, organocatalytic C3‐alkenylation of pyrroles is reported. Readily available aldehydes were employed as alkenylating agent and the reaction tolerates several key functional groups. The E‐alkenylated products were isolated in moderate to exclusive selectivity. A one‐pot two‐fold alkenylation strategy is also developed for further downstream modifications. To show the applicability, synthetically challenging indolylpyrrole derivatives were synthesized using Cadogan cyclization.
A protocol for the mechanochemical synthesis of copper(I)/N-heterocyclic carbene complexes using cheap and readily available K3PO4 as base has been developed. This method employing a ball mill is amenable to typical simple copper(I)/NHC complexes but also to a sophisticated copper(I)/N-heterocyclic carbene complex bearing a guanidine moiety. In this way, the present approach circumvents commonly employed silver(I) complexes which are associated with significant and undesired waste formation and the excessive use of solvents. The resulting bifunctional catalyst has been shown to be active in a variety of reduction/hydrogenation transformations employing dihydrogen as terminal reducing agent.
A sophisticated bifunctional catalyst bearing a copper(I)/N-heterocyclic carbene and a guanidine organocatalyst has been prepared by a mechanochemical synthesis in a ball mill. This approach circumvents commonly employed silver(I) complexes which are associated with significant and undesired waste formation. Due to the bifunctional nature of the desired complex, earlier mechanochemical conditions were not applicable and a new protocol based on cheap and readily available K3PO4 as base has been developed. The resulting complex has been shown to be active in a variety of reduction/hydrogenation transformations employing dihydrogen as terminal reducing agent.
A sophisticated bifunctional catalyst bearing a copper(I)/N-heterocyclic carbene and a guanidine organocatalyst has been prepared by a mechanochemical synthesis in a ball mill. This approach circumvents commonly employed silver(I) complexes which are associated with significant and undesired waste formation. Due to the bifunctional nature of the desired complex, earlier mechanochemical conditions were not applicable and a new protocol based on cheap and readily available K3PO4 as base has been developed. The resulting complex has been shown to be active in a variety of reduction/hydrogenation transformations employing dihydrogen as terminal reducing agent.
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