Ruthenium(II)-Mediated Carbon-Carbon Bond Formation between Acetonitrile and Pyrrole: Combined Experimental and Computational Study

Description:

This article discusses ruthenium(II)-mediated carbon-carbon bond formation between acetonitrile and pyrrole.

Creator(s):
Creation Date: September 13, 2005
Partner(s):
UNT College of Arts and Sciences
Collection(s):
UNT Scholarly Works
Usage:
Total Uses: 216
Past 30 days: 10
Yesterday: 0
Creator (Author):
Pittard, Karl A.

North Carolina State University

Creator (Author):
Cundari, Thomas R., 1964-

University of North Texas

Creator (Author):
Gunnoe, T. Brent

North Carolina State University

Creator (Author):
Day, Cynthia S.

Wake Forest University

Creator (Author):
Petersen, Jeffrey L.

West Virginia University

Publisher Info:
Publisher Name: American Chemical Society
Place of Publication: [Washington, D.C.]
Date(s):
  • Creation: September 13, 2005
Description:

This article discusses ruthenium(II)-mediated carbon-carbon bond formation between acetonitrile and pyrrole.

Degree:
Department: Chemistry
Note:

Reprinted with permission from Organometallics. Copyright 2005 American Chemical Society.

Note:

Abstract: The reaction of TpRu(CO)(NCMe)(Me) (1) and pyrrole forms TpRu(CO) {κ2-N,N-(H)N = C(Me)(NC4H3)} (2). The formation of complex 2 involves the cleavage of the N-H bond and 2-position C-H bonds of pyrrole as well as a C-C bond forming step between pyrrole and the acetonitrile ligand of 1. Mechanistic studies indicate that the most likely reaction pathway involves initial metal-mediated N-H activation of pyrrole to produce TpRu(CO)(N-pyrrolyl)-(NCMe) (3) followed by C-C bond formation and proton transfer. Complex 3 has been independently prepared and demonstrated to convert to 2. Computational studies support the suggested selectivity for initial N-H bond cleavage in preference to C-H bond activation.

Physical Description:

10 p.

Language(s):
Subject(s):
Keyword(s): bonds | transition metal complexes
Source: Organometallics, 2005, Washington DC: American Chemical Society, pp. 5015-5024
Partner:
UNT College of Arts and Sciences
Collection:
UNT Scholarly Works
Identifier:
  • DOI: 10.1021/om0506668
  • ARK: ark:/67531/metadc77184
Resource Type: Article
Format: Text
Rights:
Access: Public
Citation:
Publication Title: Organometallics
Volume: 24
Page Start: 5015
Page End: 5024
Pages: 10
Peer Reviewed: Yes