Transition-metal-catalyzed C-C bond formation via C-H activation. Intermolecular hydroacylation: The addition of aldehydes to alkenes

Todd B. Marder; D. Christopher Roe; David Milstein

Transition-metal-catalyzed C-C bond formation via C-H activation. Intermolecular hydroacylation: The addition of aldehydes to alkenes

Todd B. Marder, D. Christopher Roe, David Milstein

Weizmann Institute of Science, Israel

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

179 Citations (Scopus)

Abstract

The indenyl complex [(η⁵-C₉H₇)Rh(η²-C ₂H₄)₂] (1) is a catalyst for intermolecular hydroacylation, the addition of aldehydes to alkenes. Aldehyde decarbonylation is not a significant process with aromatic aldehydes and 1. The model system PhCHO + C₂H₄ gives propiophenone cleanly with turnover rates of up to ca. 4 h^-1 at 100°C and 1000 psi charge of C₂H₄. Deuterium-labeling studies were conducted by in situ ²H NMR spectroscopy under catalytic conditions using a specially designed high-pressure NMR tube. Other aldehydes and formates also add to ethylene using 1.

Original language	English
Pages (from-to)	1451-1453
Number of pages	3
Journal	Organometallics
Volume	7
Issue number	6
Publication status	Published - 1988

ASJC Scopus subject areas

Inorganic Chemistry
Organic Chemistry

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title = "Transition-metal-catalyzed C-C bond formation via C-H activation. Intermolecular hydroacylation: The addition of aldehydes to alkenes",

abstract = "The indenyl complex [(η5-C9H7)Rh(η2-C 2H4)2] (1) is a catalyst for intermolecular hydroacylation, the addition of aldehydes to alkenes. Aldehyde decarbonylation is not a significant process with aromatic aldehydes and 1. The model system PhCHO + C2H4 gives propiophenone cleanly with turnover rates of up to ca. 4 h-1 at 100°C and 1000 psi charge of C2H4. Deuterium-labeling studies were conducted by in situ 2H NMR spectroscopy under catalytic conditions using a specially designed high-pressure NMR tube. Other aldehydes and formates also add to ethylene using 1.",

author = "Marder, {Todd B.} and Roe, {D. Christopher} and David Milstein",

year = "1988",

language = "English",

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publisher = "American Chemical Society",

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T1 - Transition-metal-catalyzed C-C bond formation via C-H activation. Intermolecular hydroacylation

T2 - The addition of aldehydes to alkenes

AU - Marder, Todd B.

AU - Roe, D. Christopher

AU - Milstein, David

PY - 1988

Y1 - 1988

N2 - The indenyl complex [(η5-C9H7)Rh(η2-C 2H4)2] (1) is a catalyst for intermolecular hydroacylation, the addition of aldehydes to alkenes. Aldehyde decarbonylation is not a significant process with aromatic aldehydes and 1. The model system PhCHO + C2H4 gives propiophenone cleanly with turnover rates of up to ca. 4 h-1 at 100°C and 1000 psi charge of C2H4. Deuterium-labeling studies were conducted by in situ 2H NMR spectroscopy under catalytic conditions using a specially designed high-pressure NMR tube. Other aldehydes and formates also add to ethylene using 1.

AB - The indenyl complex [(η5-C9H7)Rh(η2-C 2H4)2] (1) is a catalyst for intermolecular hydroacylation, the addition of aldehydes to alkenes. Aldehyde decarbonylation is not a significant process with aromatic aldehydes and 1. The model system PhCHO + C2H4 gives propiophenone cleanly with turnover rates of up to ca. 4 h-1 at 100°C and 1000 psi charge of C2H4. Deuterium-labeling studies were conducted by in situ 2H NMR spectroscopy under catalytic conditions using a specially designed high-pressure NMR tube. Other aldehydes and formates also add to ethylene using 1.

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