Organolanthanide-catalyzed carbon-heteroatom bond formation. Observations on the facile, regiospecific cyclization of aminoalkynes

Yanwu Li; Peng Fei Fu; Tobin J Marks

Organolanthanide-catalyzed carbon-heteroatom bond formation. Observations on the facile, regiospecific cyclization of aminoalkynes

Yanwu Li, Peng Fei Fu, Tobin J Marks

Northwestern University

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

135 Citations (Scopus)

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
Pages (from-to)	439-440
Number of pages	2
Journal	Organometallics
Volume	13
Issue number	2
Publication status	Published - 1994

ASJC Scopus subject areas

Inorganic Chemistry
Organic Chemistry

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title = "Organolanthanide-catalyzed carbon-heteroatom bond formation. Observations on the facile, regiospecific cyclization of aminoalkynes",

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}",

year = "1994",

language = "English",

volume = "13",

pages = "439--440",

journal = "Organometallics",

issn = "0276-7333",

publisher = "American Chemical Society",

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T1 - Organolanthanide-catalyzed carbon-heteroatom bond formation. Observations on the facile, regiospecific cyclization of aminoalkynes

AU - Li, Yanwu

AU - Fu, Peng Fei

AU - Marks, Tobin J

PY - 1994

Y1 - 1994

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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