Solvent-dependent regiochemical cyclotrimerisation of phenylacetylene with cobalt catalysts containing disulfide ligands: A case study

被引：64

作者：

Hilt, Gerhard ^{[1
]}

Hengst, Christoph ^{[1
]}

Hess, Wilfried ^{[1
]}

机构：

[1] Univ Marburg, Fachbereich Chem, D-35043 Marburg, Germany

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2008年 / 2008卷 / 13期

关键词：

cobalt; disulfide ligands; cyclotrimerisation; regioselectivity; heterogeneous catalysis;

D O I：

10.1002/ejoc.200800106

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The intermolecular cobalt-catalysed cyclotrimerisation of phenylacetylene as a benchmark alkyne with [1,2-bis(4-methoxyphenylthio)ethane]cobalt dibromide gave the symmetrical 1,3,5-triphenylbenzene as the major product when dichloromethane was used as the solvent, whereas the unsymmetrical 1,2,4-trisubstituted product was obtained in acetonitrile in quantitative yield. Optimisation of the aromatic and aliphatic disulfide ligands in different solvents is discussed. ((c) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008).

引用

页码：2293 / 2297

页数：5

共 46 条

[1] Cobalt-catalyzed cyclotrimerization of alkynes: The answer to the puzzle of parallel reaction pathways
Agenet, Nicolas
Gandon, Vincent
Vollhardt, K. Peter C.
Malacria, Max
Aubert, Corinne
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (28) : 8860 - 8871
[2] BONNEMAN.H, 1974, SYNTHESIS-STUTTGART, P575
[3] REDUCTIVE FISSION OF METHYL SULPHIDES 1,3-DITHIOLANS AND A 1,3-OXATHIOLAN BY SODIUM IN LIQUID AMMONIA
BROWN, ED
IQBAL, SM
OWEN, LN
[J]. JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC, 1966, (04): : 415 - &
[4] Efficient intermolecular [2+2+2] alkyne cyclotrimerization in aqueous medium using a ruthenium(IV) precatalyst
Cadierno, Victorio
Garcia-Garrido, Sergio E.
Gimeno, Jose
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (47) : 15094 - 15095
[5] The cyclooligomerization of arylethynes in ionic liquids catalysed by ruthenium porphyrins: a case of real catalyst recycling
Conte, V
Elakkari, E
Floris, B
Mirruzzo, V
Tagliatesta, P
[J]. CHEMICAL COMMUNICATIONS, 2005, (12) : 1587 - 1588
[6] Formation of pyridine from acetylenes and nitriles catalyzed by RuCpCl, CoCp, and RhCp derivatives - A computational mechanistic study
Dazinger, Georg
Torres-Rodrigues, Marta
Kirchner, Karl
Calhorda, Maria Jose
Costa, Paulo J.
[J]. JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2006, 691 (21) : 4434 - 4445
[7] The first metallacyclopentadiene(alkyne) complexes and their discrete isomerization to η4-bound arenes:: The missing link in the prevalent mechanism of transition metal catalyzed alkyne cyclotrimerizations, as exemplified by cyclopentadienylcobalt
Diercks, R
Eaton, BE
Gürtzgen, S
Jalisatgi, S
Matzger, AJ
Radde, RH
Vollhardt, KPC
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (32) : 8247 - 8248
[8] Syntheses of 1,3-disilaindanes, 1,4-disilatetralines, and 1,3-disila-1,3-dihydroisobenzofuranes using cobalt-catalyzed [2+2+2] cycloadditions
Doszczak, Leszek
Tacke, Reinhold
[J]. ORGANOMETALLICS, 2007, 26 (23) : 5722 - 5723
[9] Novel ligand-free, cobalt-catalyzed [2+2+2] cycloadditions: Syntheses of 1,4-disilatetralines and 1,3-disilaindanes
Doszczak, Leszek
Fey, Philipp
Tacke, Reinhold
[J]. SYNLETT, 2007, (05) : 753 - 756
[10] Ferretti A, 1962, ORG SYNTH, V42, P22

← 1 2 3 4 5 →