New Indenylidene‐Schiff Base‐Ruthenium Complexes for Cross‐Metathesis and Ring‐Closing Metathesis

Advanced Synthesis and Catalysis - Tập 351 Số 16 - Trang 2689-2701 - 2009
Ana M. Lozano Vila1,2, Stijn Monsaert1,2, Renata Drozdzak1,2, Stanisław Wołowiec3, Francis Verpoort1,2
1Department of Inorganic and Physical Chemistry, Laboratory of Organometallic Chemistry and Catalysis, Ghent University, Krijgslaan 281 (S-3), 9000 Ghent, Belgium, Fax: (+32)-9-264-4983
2phone: (+32)-9-264-4436
3Department of General Chemistry and Electrochemistry, Rzeszow University of Technology, Al. Powstancow Warrszawy 6, PO Box 85, 35-959 Rzeszow, Poland

Tóm tắt

AbstractWe here report on the stability and catalytic activity of new indenylidene‐Schiff base‐ruthenium complexes 3a–f through representative cross‐metathesis (CM) and ring‐closing metathesis (RCM) reactions. Excellent activity of the new complexes was found for the two selected RCM reactions; prominent conversion was obtained compared to the commercial Hoveyda–Grubbs catalyst 2. Moreover, excellent results were obtained for a standard CM reaction. Higher conversions were achieved with one of the indenylidene catalysts compared with Hoveyda–Grubbs catalyst. Unexpectedly, an isomerization reaction was observed during the CM reaction of allylbenzene. To the best of our knowledge, isomerization reactions in this model CM reaction in closed systems have never been described using first generation catalysts, including the Hoveyda–Grubbs catalyst. The first model CM reactions as well as the RCM reactions have been monitored using 1H NMR. The course of the CM reaction of 3‐phenylprop‐1‐ene (8) and cis‐1,4‐diacetoxybut‐2‐ene (9) was monitored by GC. The isomerization reaction was studied by means of GC‐mass spectrometry and in situ IR spectroscopy. All catalysts were structurally characterized by means of 1H, 13C, and 31P NMR spectroscopy.

Từ khóa


Tài liệu tham khảo

10.1002/9783527619481

10.1038/nature06351

Schrodi Y., 2007, Aldrichimica Acta, 40, 45

10.1016/j.tet.2004.05.124

10.1002/ange.200500369

10.1002/anie.200500369

Monsaert S., 2009, Chem. Soc. Rev., 10

10.2478/BF02479271

10.2174/157017908786241563

 

10.1007/978-1-4020-6091-5_3

10.1016/S0040-4039(02)02247-5

10.1039/b709994k

 

10.1002/ange.19951071818

10.1002/anie.199520391

10.1021/ja952676d

10.1021/ol990909q

10.1021/ja983222u

10.1021/om970910y

10.1016/j.molcata.2006.07.006

10.1016/S0022-328X(99)00376-9

10.1002/1521-3765(20010702)7:13<2842::AID-CHEM2842>3.0.CO;2-O

10.1002/chem.200305031

10.1021/jo0477594

10.1002/1521-3757(20001002)112:19<3593::AID-ANGE3593>3.0.CO;2-M

10.1002/1521-3773(20001002)39:19<3451::AID-ANIE3451>3.0.CO;2-U

10.1021/om010599r

10.1021/ja010624k

10.1002/1521-3757(20021004)114:19<3733::AID-ANGE3733>3.0.CO;2-4

10.1002/1521-3773(20021104)41:21<4035::AID-ANIE4035>3.0.CO;2-I

10.1002/ange.200250632

10.1002/anie.200250632

10.1021/om030494j

10.1021/ja042736s

10.1021/ja027472t

10.1016/j.jorganchem.2005.07.060

10.1002/1521-3765(20011119)7:22<4811::AID-CHEM4811>3.0.CO;2-P

10.1039/a808817i

 

Monsaert S., Eur. J. Org. Chem., 2009

Monsaert S., Eur. J. Inorg. Chem., 2008

Drozdzak R., 2009, Organometallics

 

10.1016/0010-8545(93)01105-7

10.1016/j.cct.2003.09.003

10.1002/adsc.200600264

 

10.1016/j.ccr.2005.05.003

10.1002/adsc.200404389

10.1002/adsc.200700042

Vernall A. J., 2003, Aldrichimica Acta, 36, 93

10.1002/ange.200200556

10.1002/anie.200200556

10.1021/ja993063u

10.1039/b703164p

10.1021/ja0214882

10.1002/1615-4169(200208)344:6/7<728::AID-ADSC728>3.0.CO;2-4

10.1021/ja9939744

10.1039/b311496c

10.1595/147106705X24580

10.1002/chem.200600064

 

10.1016/j.tetlet.2004.10.044

10.3998/ark.5550190.0006.109

Scheinmann F., 1970, An introduction to spectroscopic methods for the identification of organic compounds, 174

 

See ref.[1a];

see ref.[1b];

see ref.[1c];

10.1021/cr020095i

10.1021/cr0200872

10.1021/cr020109k

10.1021/cr020009e

Nicolaou K. C., 2006, Angew. Chem., 118, 4564

10.1002/anie.200500369

see ref.[5]

10.1002/1615-4169(200208)344:6/7<639::AID-ADSC639>3.0.CO;2-0

Slugovc C., 2004, J. Am. Chem. Soc., 23, 3622

10.1021/om0493210

10.1021/om060091u

10.1002/ange.200454157

10.1002/anie.200454157

Thông tin
Thông tin xuất bản

Advanced Synthesis and Catalysis

Tập 351 Số 16

2689-2701

Thông tin tác giả