A highly stable adamantyl-substituted pincer-ligated iridium catalyst for alkane dehydrogenation

Benudhar Punji; Thomas J. Emge; Alan S. Goldman

doi:10.1021/om100145q

A highly stable adamantyl-substituted pincer-ligated iridium catalyst for alkane dehydrogenation

Benudhar Punji, Thomas J. Emge, Alan S. Goldman

Rutgers University

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

86 Citations (Scopus)

Abstract

The adamantyl-substituted pincer-ligand precursor ^AdPCP-H [(^AdPCP = κ³-C₆H₃-2,6-(CH ₂PAd₂)₂); Ad = 1-adamantyl] has been synthesized by the reaction of 1,3-dibromoxylene with di-1-adamantylphosphine in the presence of triethylamine. Treatment of ^AdPCP-H with [Ir(COD)Cl]₂ (COD = 1,5-cyclooctadiene) affords the pincer-ligated complex (^AdPCP)IrHCl, which was crystallographically characterized. Dehydrohalogenation of (^AdPCP)IrHCl either with LiBEt₃H or with KO^tBu, under hydrogen atmosphere, yields the hydrides ( ^AdPCP)IrH₂ and (^AdPCP)IrH₄. ( ^AdPCP)IrH₂ catalyzes dehydrogenation of alkanes with a level of activity comparable to that of the previously reported ( ^tBuPCP)IrH₂, while it is thermally much more robust than the ^tBuPCP analogue, as well as ^iPrPCP or ^tBuPOCOP pincer complexes.

Original language	English
Pages (from-to)	2702-2709
Number of pages	8
Journal	Organometallics
Volume	29
Issue number	12
DOIs	https://doi.org/10.1021/om100145q
Publication status	Published - Jun 28 2010

ASJC Scopus subject areas

Physical and Theoretical Chemistry
Organic Chemistry
Inorganic Chemistry

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title = "A highly stable adamantyl-substituted pincer-ligated iridium catalyst for alkane dehydrogenation",

abstract = "The adamantyl-substituted pincer-ligand precursor AdPCP-H [(AdPCP = κ3-C6H3-2,6-(CH 2PAd2)2); Ad = 1-adamantyl] has been synthesized by the reaction of 1,3-dibromoxylene with di-1-adamantylphosphine in the presence of triethylamine. Treatment of AdPCP-H with [Ir(COD)Cl]2 (COD = 1,5-cyclooctadiene) affords the pincer-ligated complex (AdPCP)IrHCl, which was crystallographically characterized. Dehydrohalogenation of (AdPCP)IrHCl either with LiBEt3H or with KOtBu, under hydrogen atmosphere, yields the hydrides ( AdPCP)IrH2 and (AdPCP)IrH4. ( AdPCP)IrH2 catalyzes dehydrogenation of alkanes with a level of activity comparable to that of the previously reported ( tBuPCP)IrH2, while it is thermally much more robust than the tBuPCP analogue, as well as iPrPCP or tBuPOCOP pincer complexes.",

author = "Benudhar Punji and Emge, {Thomas J.} and Goldman, {Alan S.}",

year = "2010",

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AU - Emge, Thomas J.

AU - Goldman, Alan S.

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Y1 - 2010/6/28

N2 - The adamantyl-substituted pincer-ligand precursor AdPCP-H [(AdPCP = κ3-C6H3-2,6-(CH 2PAd2)2); Ad = 1-adamantyl] has been synthesized by the reaction of 1,3-dibromoxylene with di-1-adamantylphosphine in the presence of triethylamine. Treatment of AdPCP-H with [Ir(COD)Cl]2 (COD = 1,5-cyclooctadiene) affords the pincer-ligated complex (AdPCP)IrHCl, which was crystallographically characterized. Dehydrohalogenation of (AdPCP)IrHCl either with LiBEt3H or with KOtBu, under hydrogen atmosphere, yields the hydrides ( AdPCP)IrH2 and (AdPCP)IrH4. ( AdPCP)IrH2 catalyzes dehydrogenation of alkanes with a level of activity comparable to that of the previously reported ( tBuPCP)IrH2, while it is thermally much more robust than the tBuPCP analogue, as well as iPrPCP or tBuPOCOP pincer complexes.

AB - The adamantyl-substituted pincer-ligand precursor AdPCP-H [(AdPCP = κ3-C6H3-2,6-(CH 2PAd2)2); Ad = 1-adamantyl] has been synthesized by the reaction of 1,3-dibromoxylene with di-1-adamantylphosphine in the presence of triethylamine. Treatment of AdPCP-H with [Ir(COD)Cl]2 (COD = 1,5-cyclooctadiene) affords the pincer-ligated complex (AdPCP)IrHCl, which was crystallographically characterized. Dehydrohalogenation of (AdPCP)IrHCl either with LiBEt3H or with KOtBu, under hydrogen atmosphere, yields the hydrides ( AdPCP)IrH2 and (AdPCP)IrH4. ( AdPCP)IrH2 catalyzes dehydrogenation of alkanes with a level of activity comparable to that of the previously reported ( tBuPCP)IrH2, while it is thermally much more robust than the tBuPCP analogue, as well as iPrPCP or tBuPOCOP pincer complexes.

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