Formation of Di-tert-butylurea from a Mononuclear Iron Tris(isocyanide) Complex

Anitha S. Gowda; Andreas Baur; Carl A. Scaggs; Jeffrey L. Petersen; Jessica M. Hoover

doi:10.1021/acs.organomet.6b00687

Formation of Di-tert-butylurea from a Mononuclear Iron Tris(isocyanide) Complex

Anitha S. Gowda, Andreas Baur, Carl A. Scaggs, Jeffrey L. Petersen, Jessica M. Hoover

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Abstract

We report the synthesis and characterization of the tripodal iron tris(isocyanide) complexes [Tm^R′Fe(CNR)₃](OTf) (R = tBu, Ad; R′ = Me, Ph, Mes). These complexes generate the corresponding disubstituted ureas when treated sequentially with a reductant (KC₈) and a proton source (H₂O). A series of labeling experiments indicate air to be the source of the urea oxygen, while the urea carbon is derived from the isocyanide. Crossover experiments indicate a key role for H₂NR in the formation of the disubstituted urea, and we propose a pathway for urea formation that involves a diaminocarbene intermediate that is formed from H₂NR attack on a bound isocyanide ligand.

Original language	English (US)
Pages (from-to)	3720-3727
Number of pages	8
Journal	Organometallics
Volume	35
Issue number	21
DOIs	https://doi.org/10.1021/acs.organomet.6b00687
State	Published - Nov 14 2016
Externally published	Yes

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© 2016 American Chemical Society.

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title = "Formation of Di-tert-butylurea from a Mononuclear Iron Tris(isocyanide) Complex",

abstract = "We report the synthesis and characterization of the tripodal iron tris(isocyanide) complexes [TmR′Fe(CNR)3](OTf) (R = tBu, Ad; R′ = Me, Ph, Mes). These complexes generate the corresponding disubstituted ureas when treated sequentially with a reductant (KC8) and a proton source (H2O). A series of labeling experiments indicate air to be the source of the urea oxygen, while the urea carbon is derived from the isocyanide. Crossover experiments indicate a key role for H2NR in the formation of the disubstituted urea, and we propose a pathway for urea formation that involves a diaminocarbene intermediate that is formed from H2NR attack on a bound isocyanide ligand.",

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T1 - Formation of Di-tert-butylurea from a Mononuclear Iron Tris(isocyanide) Complex

AU - Gowda, Anitha S.

AU - Baur, Andreas

AU - Scaggs, Carl A.

AU - Petersen, Jeffrey L.

AU - Hoover, Jessica M.

PY - 2016/11/14

Y1 - 2016/11/14

N2 - We report the synthesis and characterization of the tripodal iron tris(isocyanide) complexes [TmR′Fe(CNR)3](OTf) (R = tBu, Ad; R′ = Me, Ph, Mes). These complexes generate the corresponding disubstituted ureas when treated sequentially with a reductant (KC8) and a proton source (H2O). A series of labeling experiments indicate air to be the source of the urea oxygen, while the urea carbon is derived from the isocyanide. Crossover experiments indicate a key role for H2NR in the formation of the disubstituted urea, and we propose a pathway for urea formation that involves a diaminocarbene intermediate that is formed from H2NR attack on a bound isocyanide ligand.

AB - We report the synthesis and characterization of the tripodal iron tris(isocyanide) complexes [TmR′Fe(CNR)3](OTf) (R = tBu, Ad; R′ = Me, Ph, Mes). These complexes generate the corresponding disubstituted ureas when treated sequentially with a reductant (KC8) and a proton source (H2O). A series of labeling experiments indicate air to be the source of the urea oxygen, while the urea carbon is derived from the isocyanide. Crossover experiments indicate a key role for H2NR in the formation of the disubstituted urea, and we propose a pathway for urea formation that involves a diaminocarbene intermediate that is formed from H2NR attack on a bound isocyanide ligand.

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Formation of Di-tert-butylurea from a Mononuclear Iron Tris(isocyanide) Complex

Abstract

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