Organolanthanide-Catalyzed Carbon–Heteroatom Bond Formation. Observations on the Facile, Regiospecific Cyclization of Aminoalkynes

Yanwu Li; Peng Fei Fu; Tobin J. Marks

doi:10.1021/om00014a015

Organolanthanide-Catalyzed Carbon–Heteroatom Bond Formation. Observations on the Facile, Regiospecific Cyclization of Aminoalkynes

Yanwu Li, Peng Fei Fu, Tobin J. Marks^*

^*Corresponding author for this work

Chemistry

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

137 Scopus citations

Abstract

The organolanthanide complex (η⁵-Me₅C₅)₂-SmCH(TMS)₂ serves as a precatalyst for the efficient and regiospecific hydroamination/cyclization of aliphatic and aromatic aminoalkynes RC≡C(CH₂)_nNH₂ to yield the corresponding heterocycles RCH₂C=N(CH₂)_n-1CH₂. Kinetic and mechanistic evidence argues that the turnover-limiting step is intramolecular alkyne insertion into the Sm—N bond followed by rapid protonolysis of the resulting Sm—C bond.

Original language	English (US)
Pages (from-to)	439-440
Number of pages	2
Journal	Organometallics
Volume	13
Issue number	2
DOIs	https://doi.org/10.1021/om00014a015
State	Published - Feb 1 1994

ASJC Scopus subject areas

Physical and Theoretical Chemistry
Organic Chemistry
Inorganic Chemistry

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abstract = "The organolanthanide complex (η5-Me5C5)2-SmCH(TMS)2 serves as a precatalyst for the efficient and regiospecific hydroamination/cyclization of aliphatic and aromatic aminoalkynes RC≡C(CH2)nNH2 to yield the corresponding heterocycles RCH2C=N(CH2)n-1CH2. Kinetic and mechanistic evidence argues that the turnover-limiting step is intramolecular alkyne insertion into the Sm—N bond followed by rapid protonolysis of the resulting Sm—C bond.",

author = "Yanwu Li and Fu, {Peng Fei} and Marks, {Tobin J.}",

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AU - Fu, Peng Fei

AU - Marks, Tobin J.

PY - 1994/2/1

Y1 - 1994/2/1

N2 - The organolanthanide complex (η5-Me5C5)2-SmCH(TMS)2 serves as a precatalyst for the efficient and regiospecific hydroamination/cyclization of aliphatic and aromatic aminoalkynes RC≡C(CH2)nNH2 to yield the corresponding heterocycles RCH2C=N(CH2)n-1CH2. Kinetic and mechanistic evidence argues that the turnover-limiting step is intramolecular alkyne insertion into the Sm—N bond followed by rapid protonolysis of the resulting Sm—C bond.

AB - The organolanthanide complex (η5-Me5C5)2-SmCH(TMS)2 serves as a precatalyst for the efficient and regiospecific hydroamination/cyclization of aliphatic and aromatic aminoalkynes RC≡C(CH2)nNH2 to yield the corresponding heterocycles RCH2C=N(CH2)n-1CH2. Kinetic and mechanistic evidence argues that the turnover-limiting step is intramolecular alkyne insertion into the Sm—N bond followed by rapid protonolysis of the resulting Sm—C bond.

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Organolanthanide-Catalyzed Carbon–Heteroatom Bond Formation. Observations on the Facile, Regiospecific Cyclization of Aminoalkynes

Abstract

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