Experimental and Computational Studies of Ruthenium(II)-Catalyzed Addition of Arene C-H Bonds to Olefins

Description:

This article discusses experimental and computational studies of Ruthenium(II)-Catalyzed addition of arene C-H bonds to olefins.

Creator(s):
Creation Date: September 10, 2004
Partner(s):
UNT College of Arts and Sciences
Collection(s):
UNT Scholarly Works
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Lail, Marty

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Bell, Christen M.

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Conner, David

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Cundari, Thomas R., 1964-

University of North Texas

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Gunnoe, T. Brent

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Petersen, Jeffrey L.

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Publisher Info:
Publisher Name: American Chemical Society
Place of Publication: [Washington, DC]
Date(s):
  • Creation: September 10, 2004
Description:

This article discusses experimental and computational studies of Ruthenium(II)-Catalyzed addition of arene C-H bonds to olefins.

Degree:
Department: Chemistry
Note:

Reprinted with permission from Organometallics. Copyright 2004 American Chemical Society.

Note:

Abstract: Hydroarylation reactions of olefins are catalyzed by the octahedral Ru(II) complex TpRu-(CO)(NCMe)(Ph) (1) (Tp = hydridotris(pyrazolyl)borate). Experimental studies and density functional theory calculations support a reaction pathway that involves initial acetonitrile/olefin ligand exchange and subsequent olefin insertion into the ruthenium-phenyl bond. Metal-mediated C-H activation of arene to form a Ru-aryl bond with release of alkyl arene completes the proposed catalytic cycle. The cyclopentadienyl complex CpRu(PPh3)2(Ph) produces ethylbenzene and styrene from a benzene/ethylene solution at 90 ˚C; however, the transformation is not catalytic. A benzene solution of (PCP)Ru(CO)(Ph) (PCP = 2,6-)CH2Pt-Bu2)2C6H3) and ethylene at 90 ˚C produces styrene in 12% yield without observation of ethylbenzene. Computational studies (DFT) suggest that the C-H activation step does not proceed through the formation of a Ru(IV) oxidative addition intermediate but rather occurs by a concerted pathway.

Physical Description:

14 p.

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Subject(s):
Keyword(s): olefins | reaction pathways | ruthenium
Source: Organometallics, 2004, Washington DC: American Chemical Society, pp. 5007-5020
Partner:
UNT College of Arts and Sciences
Collection:
UNT Scholarly Works
Identifier:
  • DOI: 10.1021/om049404g
  • ARK: ark:/67531/metadc77180
Resource Type: Article
Format: Text
Rights:
Access: Public
Citation:
Publication Title: Organometallics
Volume: 23
Page Start: 5007
Page End: 5020
Pages: 14
Peer Reviewed: Yes