P,N-type phosphaalkene-based Ir(<scp>i</scp>) complexes: synthesis, coordination chemistry, and catalytic applications

Gupta, Priyanka; Drexler, Hans‐Joachim; Wingad, Richard L.; Wass, Duncan F.; Baráth, Eszter; Beweries, Torsten; Hering‐Junghans, Christian

doi:10.1039/d3qi00142c

“…selectivity, TOF) are targeted, this performance is similar to the best existing examples. 29–33,39,43…”

Section: Resultsmentioning

confidence: 99%

“…24 The reaction pathway includes dehydrogenation of simple alcohol, base-catalyzed aldol condensation reaction and rehydrogenation of the aldol product. 25 Our group 26–33 and others 34–49 have been seeking new homogeneous catalysts for ethanol upgrading via Guerbet chemistry. Despite these recent advances, there is still significant scope for further catalyst development.…”

Section: Introductionmentioning

confidence: 99%

Backbone-functionalised ruthenium diphosphine complexes for catalytic upgrading of ethanol and methanol to iso-butanol

Sama,

Doyle,

Kariuki

et al. 2024

Dalton Trans.

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Die Azid‐Wittig Reaktion

Kushik,

Petrov,

Ranieri

et al. 2024

Angewandte Chemie

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The introduction of heteroatoms into conjugated organic molecules is an important strategy to tune their reactivity and physical properties. In this realm triazabutadienes (TBDs) of the general from R2C=N−N=NR’ are an interesting class of compounds, however, general synthetic protocols for their generation are limited. Based on the serendipitous finding that the sterically encumbered azide Mes*N3 (Mes* = 2,4,6‐tBu3C6H2) reacted with PMe3 in the presence of an aromatic aldehyde to form a TBD, we now report on the “Azide‐Wittig” reaction. This azide‐Wittig reaction is shown to be a versatile tool for the synthesis of a variety of TBDs, tolerating a wide range of aldehydes and organic azides as coupling partners. The preference for azide‐Wittig, rather than aza‐Wittig reactivity was rationalized using computational methods. This study shows how kinetic control can significantly alter the reaction pathway, thereby switching from an aza‐Wittig to an azide‐Wittig regime.

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The Azide‐Wittig Reaction

Kushik,

Petrov,

Ranieri

et al. 2024

Angew Chem Int Ed

0

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The introduction of heteroatoms into conjugated organic molecules is an important strategy to tune their reactivity and physical properties. In this realm triazabutadienes (TBDs) of the general from R2C=N−N=NR’ are an interesting class of compounds, however, general synthetic protocols for their generation are limited. Based on the serendipitous finding that the sterically encumbered azide Mes*N3 (Mes* = 2,4,6‐tBu3C6H2) reacted with PMe3 in the presence of an aromatic aldehyde to form a TBD, we now report on the “Azide‐Wittig” reaction. This azide‐Wittig reaction is shown to be a versatile tool for the synthesis of a variety of TBDs, tolerating a wide range of aldehydes and organic azides as coupling partners. The preference for azide‐Wittig, rather than aza‐Wittig reactivity was rationalized using computational methods. This study shows how kinetic control can significantly alter the reaction pathway, thereby switching from an aza‐Wittig to an azide‐Wittig regime.

show abstract

P,N-type phosphaalkene-based Ir(i) complexes: synthesis, coordination chemistry, and catalytic applications

Abstract: Phosphaalkenes are an emerging class of ligands with unique electronic properties that can be regarded as tuneable variants of the ubiquitous CO ligand. Our group has recently reported the synthesis...

Cited by 7 publications

References 75 publications

Backbone-functionalised ruthenium diphosphine complexes for catalytic upgrading of ethanol and methanol to iso-butanol

Backbone-functionalised ruthenium diphosphine complexes for catalytic upgrading of ethanol and methanol to iso-butanol

Die Azid‐Wittig Reaktion

The Azide‐Wittig Reaction

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