Ruthenium induced C-N bond activation of an N-heterocyclic carbene: Isolation of C- and N-bound tautomers

被引:162
作者
Burling, Suzanne [1 ]
Mahon, Mary F. [1 ]
Powell, Rachael E. [1 ]
Whittlesey, Michael K. [1 ]
Williams, Jonathan M. J. [1 ]
机构
[1] Univ Bath, Dept Chem, Bath BA2 7AY, Avon, England
基金
英国工程与自然科学研究理事会;
关键词
D O I
10.1021/ja065582k
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
C-N bond activation of the N-heterocyclic carbene 1,3-diisopropyl-4,5-dimethylimidazol-2-ylidene occurs with Ru(PPh3)3(CO)HCl to give the C-2 bound 1-isopropyl-4,5-dimethylimidazol-2-ylidene complex Ru(C-IiPrHMe2)(PPh3)2(CO)HCl via loss of propene. In the presence of free carbene, this undergoes tautomerism to the corresponding imidazole compound Ru(N-IiPrHMe2)(PPh3)2(CO)HCl. Copyright © 2006 American Chemical Society.
引用
收藏
页码:13702 / 13703
页数:2
相关论文
共 26 条
[11]   N-heterocyclic pincer dicarbene complexes of iron(II): C-2 and C-5 metalated carbenes on the same metal center [J].
Danopoulos, AA ;
Tsoureas, N ;
Wright, JA ;
Light, ME .
ORGANOMETALLICS, 2004, 23 (02) :166-168
[12]   Carbon monoxide-promoted carbene insertion into the aryl substituent of an N-heterocyclic carbene ligand: Buchner reaction in a ruthenium carbene complex [J].
Galan, BR ;
Gembicky, M ;
Dominiak, PM ;
Keister, JB ;
Diver, ST .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (45) :15702-15703
[13]  
Graham DC, 2006, DALTON T, P1768, DOI 10.1039/b512681a
[14]   Abnormal ligand binding and reversible ring hydrogenation in the reaction of imidazolium salts with IrH5(PPh3)2 [J].
Gründemann, S ;
Kovacevic, A ;
Albrecht, M ;
Faller, JW ;
Crabtree, RH .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (35) :10473-10481
[15]   Synthesis of new iridium N-heterocyclic carbene complexes and facile intramolecular alkyl C-H bond activation reactions of the carbene ligand [J].
Hanasaka, F ;
Tanabe, Y ;
Fujita, K ;
Yamaguchi, R .
ORGANOMETALLICS, 2006, 25 (04) :826-831
[16]   Structure and reactivity of "unusual" N-heterocyclic carbene (NHC) palladium complexes synthesized from imidazolium salts [J].
Lebel, H ;
Janes, MK ;
Charette, AB ;
Nolan, SP .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (16) :5046-5047
[17]   Kinetic and density functional studies on alkyl-carbene elimination from PdII heterocylic carbene complexes:: A new type of reductive elimination with clear implications for catalysis [J].
McGuinness, DS ;
Saendig, N ;
Yates, BF ;
Cavell, KJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (17) :4029-4040
[18]   CONVERSION OF IMIDAZOLE INTO MU-2,3-DIHYDRO-1H-IMIDAZOLE-1,2,2-TRIYL LIGANDS [J].
MULLER, J ;
STOCK, R .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1983, 22 (12) :993-993
[19]  
Nolan S.P., 2006, N-Heterocyclic Carbenes in Synthesis, DOI DOI 10.2174/1570180813666160826100158
[20]   An electron-deficient Iridium(III) dihydride complex capable of intramolecular C-H activation [J].
Scott, NM ;
Pons, V ;
Stevens, ED ;
Heinekey, DM ;
Nolan, SP .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (17) :2512-2515