Aminotroponate zinc complexes as catalysts for the intramolecular hydroamination of alkenes and alkynes

Nils Meyer; Karolin Löhnwitz; Peter W. Roesky; Maximilian Dochnahl; Siegfried Blechert

doi:10.1021/om060369i

Aminotroponate zinc complexes as catalysts for the intramolecular hydroamination of alkenes and alkynes

Nils Meyer, Karolin Löhnwitz, Agustino, Peter W. Roesky, Maximilian Dochnahl, Siegfried Blechert

Department of Chemistry

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

64 Citations (Scopus)

Abstract

The dimeric complexes 2-(isopropylamino)troponate zinc methyl and ethyl [(iPrAT)Zn-R]₂ (R = Me (2a), Et (2b)) were synthesized by reaction of (iPrAT)H with dimethyl and diethyl zinc, respectively, in toluene at low temperature. Reacting (iPrAT)H with dimethyl zinc at elevated temperature resulted in the double-substituted complex [(iPrAT)₂Zn] (3). Compounds 2a,b, which were investigated by single-crystal X-ray diffraction, are dimeric in the solid state. The metal centers are bridged asymmetrically by two (μ)-oxygen atoms; thus a flat Zn-O-Zn'-O' plane is observed. Compounds 2a,b were used as the catalyst in the intramolecular hydroamination reaction of nonactivated terminal aminoolefins and one aminoalkyne. Good catalytic activities at elevated temperature were observed.

Original language	English
Pages (from-to)	3730-3734
Number of pages	5
Journal	Organometallics
Volume	25
Issue number	15
DOIs	https://doi.org/10.1021/om060369i
Publication status	Published - 17 Jul 2006

Access to Document

10.1021/om060369i

Cite this

@article{cee95bde58e640de8c1058f21ff86f43,

title = "Aminotroponate zinc complexes as catalysts for the intramolecular hydroamination of alkenes and alkynes",

abstract = "The dimeric complexes 2-(isopropylamino)troponate zinc methyl and ethyl [(iPrAT)Zn-R]2 (R = Me (2a), Et (2b)) were synthesized by reaction of (iPrAT)H with dimethyl and diethyl zinc, respectively, in toluene at low temperature. Reacting (iPrAT)H with dimethyl zinc at elevated temperature resulted in the double-substituted complex [(iPrAT)2Zn] (3). Compounds 2a,b, which were investigated by single-crystal X-ray diffraction, are dimeric in the solid state. The metal centers are bridged asymmetrically by two (μ)-oxygen atoms; thus a flat Zn-O-Zn'-O' plane is observed. Compounds 2a,b were used as the catalyst in the intramolecular hydroamination reaction of nonactivated terminal aminoolefins and one aminoalkyne. Good catalytic activities at elevated temperature were observed.",

author = "Nils Meyer and Karolin L{\"o}hnwitz and Agustino and Roesky, {Peter W.} and Maximilian Dochnahl and Siegfried Blechert",

year = "2006",

month = jul,

day = "17",

doi = "10.1021/om060369i",

language = "English",

volume = "25",

pages = "3730--3734",

journal = "Organometallics",

issn = "0276-7333",

publisher = "American Chemical Society",

number = "15",

}

TY - JOUR

T1 - Aminotroponate zinc complexes as catalysts for the intramolecular hydroamination of alkenes and alkynes

AU - Meyer, Nils

AU - Löhnwitz, Karolin

AU - Agustino, null

AU - Roesky, Peter W.

AU - Dochnahl, Maximilian

AU - Blechert, Siegfried

PY - 2006/7/17

Y1 - 2006/7/17

N2 - The dimeric complexes 2-(isopropylamino)troponate zinc methyl and ethyl [(iPrAT)Zn-R]2 (R = Me (2a), Et (2b)) were synthesized by reaction of (iPrAT)H with dimethyl and diethyl zinc, respectively, in toluene at low temperature. Reacting (iPrAT)H with dimethyl zinc at elevated temperature resulted in the double-substituted complex [(iPrAT)2Zn] (3). Compounds 2a,b, which were investigated by single-crystal X-ray diffraction, are dimeric in the solid state. The metal centers are bridged asymmetrically by two (μ)-oxygen atoms; thus a flat Zn-O-Zn'-O' plane is observed. Compounds 2a,b were used as the catalyst in the intramolecular hydroamination reaction of nonactivated terminal aminoolefins and one aminoalkyne. Good catalytic activities at elevated temperature were observed.

AB - The dimeric complexes 2-(isopropylamino)troponate zinc methyl and ethyl [(iPrAT)Zn-R]2 (R = Me (2a), Et (2b)) were synthesized by reaction of (iPrAT)H with dimethyl and diethyl zinc, respectively, in toluene at low temperature. Reacting (iPrAT)H with dimethyl zinc at elevated temperature resulted in the double-substituted complex [(iPrAT)2Zn] (3). Compounds 2a,b, which were investigated by single-crystal X-ray diffraction, are dimeric in the solid state. The metal centers are bridged asymmetrically by two (μ)-oxygen atoms; thus a flat Zn-O-Zn'-O' plane is observed. Compounds 2a,b were used as the catalyst in the intramolecular hydroamination reaction of nonactivated terminal aminoolefins and one aminoalkyne. Good catalytic activities at elevated temperature were observed.

UR - http://www.scopus.com/inward/record.url?scp=33746442901&partnerID=8YFLogxK

U2 - 10.1021/om060369i

DO - 10.1021/om060369i

M3 - Article

AN - SCOPUS:33746442901

SN - 0276-7333

VL - 25

SP - 3730

EP - 3734

JO - Organometallics

JF - Organometallics

IS - 15

ER -

Aminotroponate zinc complexes as catalysts for the intramolecular hydroamination of alkenes and alkynes

Abstract

Access to Document

Other files and links

Fingerprint

Cite this