TiIV-mediated reactions between primary amines and secondary carboxamides: amidine formation versus transamidation.

Content Provider	Semantic Scholar
Author	Kissounko, Denis A. Hoerter, Justin M. Guzei, Ilia A. Cui, Qiang Stahl, Shannon S.
Copyright Year	2007
Abstract	Titanium(IV)-mediated reactions between primary amines and secondary carboxamides exhibit different outcomes, amidine formation versus transamidation, depending on the identity of the TiIV complex used and the reaction conditions employed. The present study probes the origin of this divergent behavior. We find that stoichiometric TiIV, either Cp*TiIV complexes or Ti(NMe2)4, promotes formation of amidine and oxotitanium products. Under catalytic conditions, however, the outcome depends on the identity of the TiIV complex. Competitive amidine formation and transamidation are observed with Cp*TiIV complexes, generally favoring amidine formation. In contrast, the use of catalytic Ti(NMe2)4 (< or =20 mol %) results in highly selective transamidation. The ability of TiIV to avoid irreversible formation of oxotitanium products under the latter conditions has important implications for the use of TiIV in catalytic reactions.
File Format	PDF HTM / HTML
Alternate Webpage(s)	http://stahl.chem.wisc.edu/sites/stahl.chem.wisc.edu/files/publications/2007-JACS1776.pdf
Alternate Webpage(s)	http://www.chem.wisc.edu/~cui/pdf_fls/ti_iv_80.pdf
PubMed reference number	17284008v1
Volume Number	129
Issue Number	6
Journal	Journal of the American Chemical Society
Language	English
Access Restriction	Open
Subject Keyword	Addison Disease Amidines Amidone brand of methadone Amines DUOXA1 gene
Content Type	Text
Resource Type	Article