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?-Amidoaldehydes as Substrates in Rhodium-Catalyzed Intermolecular Alkyne Hydroacylation: The Synthesis of ?-Amidoketones.

ABSTRACT: We show that readily available ?-amidoaldehydes are effective substrates for intermolecular Rh-catalyzed alkyne hydroacylation reactions. The catalyst [Rh(dppe)(C6 H5 F)][BArF 4 ] provides good reactivity, and allows a broad range of aldehydes and alkynes to be used as substrates, delivering ?-amidoketone products. High yields and high levels of regioselectivity are achieved. The use of ?-amidoaldehydes as substrates establishes that 1,4-dicarbonyl motifs can be used as controlling groups in Rh-catalyzed hydroacylation reactions.

SUBMITTER: Pal R

PROVIDER: S-EPMC7540332 | biostudies-literature | 2020 Sep

REPOSITORIES: biostudies-literature

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α-Amidoaldehydes as Substrates in Rhodium-Catalyzed Intermolecular Alkyne Hydroacylation: The Synthesis of α-Amidoketones.

Pal Ritashree R O'Brien Sean C SC Willis Michael C MC

Chemistry (Weinheim an der Bergstrasse, Germany) 20200730 51

We show that readily available α-amidoaldehydes are effective substrates for intermolecular Rh-catalyzed alkyne hydroacylation reactions. The catalyst [Rh(dppe)(C6 H5 F)][BArF 4 ] provides good reactivity, and allows a broad range of aldehydes and alkynes to be used as substrates, delivering α-amidoketone products. High yields and high levels of regioselectivity are achieved. The use of α-amidoaldehydes as substrates establishes that 1,4-dicarbonyl mot ...[more]

PMID: 32449532

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