Substituent effects in ugi-smiles reactions

Nicolas Chéron; Romain Ramozzi; Laurent El Kaïm; Laurence Grimaud; Paul Fleurat-Lessard

doi:10.1021/jp4052227

Substituent effects in ugi-smiles reactions

Nicolas Chéron
, Romain Ramozzi
, Laurent El Kaïm
, Laurence Grimaud
, Paul Fleurat-Lessard

Research output: Contribution to journal › Article › peer-review

Abstract

In a recent communication, we described the mechanism of the well-known Ugi-type reactions with a model system (J. Org. Chem. 2012, 77, 1361-1366). Herein, focusing on the Ugi-Smiles coupling, we study the effects of each of the four reactants on the energy profile to further explain the experimental results. The variations observed with different carbonyl compounds rely on their influence on the formation of the aryl-imidate, whereas the variations on the amine preferentially affect the Smiles rearrangement. The effect of substituents on the phenol derivative is seen upon both aryl-imidate formation and the rearrangement. The effect of the isocyanide substituents is less pronounced.

Original language	English
Pages (from-to)	8035-8042
Number of pages	8
Journal	Journal of Physical Chemistry A
Volume	117
Issue number	33
DOIs	https://doi.org/10.1021/jp4052227
Publication status	Published - 22 Aug 2013
Externally published	Yes

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title = "Substituent effects in ugi-smiles reactions",

abstract = "In a recent communication, we described the mechanism of the well-known Ugi-type reactions with a model system (J. Org. Chem. 2012, 77, 1361-1366). Herein, focusing on the Ugi-Smiles coupling, we study the effects of each of the four reactants on the energy profile to further explain the experimental results. The variations observed with different carbonyl compounds rely on their influence on the formation of the aryl-imidate, whereas the variations on the amine preferentially affect the Smiles rearrangement. The effect of substituents on the phenol derivative is seen upon both aryl-imidate formation and the rearrangement. The effect of the isocyanide substituents is less pronounced.",

author = "Nicolas Ch{\'e}ron and Romain Ramozzi and \{El Ka{\"i}m\}, Laurent and Laurence Grimaud and Paul Fleurat-Lessard",

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doi = "10.1021/jp4052227",

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T1 - Substituent effects in ugi-smiles reactions

AU - Chéron, Nicolas

AU - Ramozzi, Romain

AU - El Kaïm, Laurent

AU - Grimaud, Laurence

AU - Fleurat-Lessard, Paul

PY - 2013/8/22

Y1 - 2013/8/22

N2 - In a recent communication, we described the mechanism of the well-known Ugi-type reactions with a model system (J. Org. Chem. 2012, 77, 1361-1366). Herein, focusing on the Ugi-Smiles coupling, we study the effects of each of the four reactants on the energy profile to further explain the experimental results. The variations observed with different carbonyl compounds rely on their influence on the formation of the aryl-imidate, whereas the variations on the amine preferentially affect the Smiles rearrangement. The effect of substituents on the phenol derivative is seen upon both aryl-imidate formation and the rearrangement. The effect of the isocyanide substituents is less pronounced.

AB - In a recent communication, we described the mechanism of the well-known Ugi-type reactions with a model system (J. Org. Chem. 2012, 77, 1361-1366). Herein, focusing on the Ugi-Smiles coupling, we study the effects of each of the four reactants on the energy profile to further explain the experimental results. The variations observed with different carbonyl compounds rely on their influence on the formation of the aryl-imidate, whereas the variations on the amine preferentially affect the Smiles rearrangement. The effect of substituents on the phenol derivative is seen upon both aryl-imidate formation and the rearrangement. The effect of the isocyanide substituents is less pronounced.

U2 - 10.1021/jp4052227

DO - 10.1021/jp4052227

M3 - Article

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VL - 117

SP - 8035

EP - 8042

JO - Journal of Physical Chemistry A

JF - Journal of Physical Chemistry A

IS - 33

ER -

Substituent effects in ugi-smiles reactions

Abstract

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