+ Resolve Article
+ Follow Us
Follow on FacebookFollow on Facebook
Follow on TwitterFollow on Twitter

+ Translate
+ Subscribe to Site Feed
GeoScience Most Shared ContentMost Shared Content

Comparison of the catalytic activity for the Suzuki-Miyaura reaction of (η(5)-Cp)Pd(IPr)Cl with (η(3)-cinnamyl)Pd(IPr)(Cl) and (η(3)-1-t-Bu-indenyl)Pd(IPr)(Cl)

, : Comparison of the catalytic activity for the Suzuki-Miyaura reaction of (η(5)-Cp)Pd(IPr)Cl with (η(3)-cinnamyl)Pd(IPr)(Cl) and (η(3)-1-t-Bu-indenyl)Pd(IPr)(Cl). Beilstein Journal of Organic Chemistry 11: 2476-2486

Complexes of the type (η(3)-allyl)Pd(L)(Cl) and (η(3)-indenyl)Pd(L)(Cl) are highly active precatalysts for the Suzuki-Miyaura reaction. Even though allyl and indenyl ligands are similar to cyclopentadienyl (Cp) ligands, there have been no detailed comparative studies exploring the activity of precatalysts of the type (η(5)-Cp)Pd(L)(Cl) for Suzuki-Miyaura reactions. Here, we compare the catalytic activity of (η(5)-Cp)Pd(IPr)(Cl) (IPr = 1,3-bis(2,6-diisopropylphenyl)-1,3-dihydro-2H-imidazol-2-ylidene, Cp) with two commercially available catalysts (η(3)-cinnamyl)Pd(IPr)(Cl) (Cin) and (η(3)-1-t-Bu-indenyl)Pd(IPr)(Cl) ( (tBu) Ind). We show that Cp gives slightly better catalytic activity than Cin, but significantly inferior activity than (tBu) Ind. This order of activity is rationalized by comparing the rates at which the precatalysts are activated to the monoligated Pd(0) active species along with the tendency of the starting precatalysts to comproportionate with monoligated Pd(0) to form inactive Pd(I) dimers. As part of this work the Cp supported Pd(I) dimer (μ-Cp)(μ-Cl)Pd2(IPr)2 (Cp (Dim) ) was synthesized and crystallographically characterized. It does not readily disproportionate to form monoligated Pd(0) and consequently Cp (Dim) is a poor catalyst for the Suzuki-Miyaura reaction.


PMID: 26732227

DOI: 10.3762/bjoc.11.269

Other references

Verburg, N.; Pouwels, P.J.W.; Boellaard, R.; Barkhof, F.; Hoekstra, O.S.; Reijneveld, J.C.; Vandertop, W.Peter.; Wesseling, P.; de Witt Hamer, P.C., 2016: Accurate Delineation of Glioma Infiltration by Advanced PET/MR Neuro-Imaging (FRONTIER Study): A Diagnostic Study Protocol. Glioma imaging, used for diagnostics, treatment planning, and follow-up, is currently based on standard magnetic resonance imaging (MRI) modalities (T1 contrast-enhancement for gadolinium-enhancing gliomas and T2 fluid-attenuated inversion recover...

Suzuki, I.; Honma, H.; Watanabe, N.; Matsubara, S.; Koyama, T., 1998: A study of neuroleptic malignant syndrome in the presenium and senium. Recently, with the increase in elderly population, we have had more opportunities to administer neuroleptics to elderly patients for hallucinatory delusional state, delirium, psychomotor excitement, wandering etc. However, little is known about th...

Doddamani, D.; Hemal, A.K.; Ansari, M.S., 2001: Ureteral stent: Help or hindrance? In healing of post traumatic nephrocutaneous fistula. Nephrocutaneous fistulas are rare complications of blunt or penetrating renal trauma. The majority are managed conservatively, some may require percutaneous drainage or ureteral stenting and some require operative intervention. Diversion of the ur...

Her C., 1992: Comparison of calculated and measured pulmonary artery systolic storage volume. Anesthesiology (Hagerstown) 77(3A): A231

Bockstael, Ne, 1987: Economic efficiency issues of grading and minimum quality standards. Economic efficiency in agricultural and food marketing edited by Richard L Kilmer and Walter J Armbruster: 250

Klimek, L.; Stuck, B.; Hundorf, J.; Schneider Gene, S.; Hoermann, K., 2001: Monophosphoryl lipid A has Th1 stimulating properties in immunotherapy with birch pollen allergoid. Allergy (Copenhagen) 56(Supplement 68): 93

Wuschech, H.; Kohler, W.; Friedel, W.; Welsch, G., 1964: Behaviour of free fatty acids in plasma after physical work. Blood was taken from the cubital vein of 7 young men immediately before and about 45 min after the end of a bicycle training race of 100 km. Free fatty acids increased highly significantly, on average by 0.67 m-equiv. per litre, in one man to a va...

Esanu, V., 1967: Absorption and distribution of P32 in the roots of Tobacco infected with Tobacco mosaic virus. In plants inoculated at the 6-7-leaf stage and grown in different nutrient sols, with added P32 entry of P32 into the roots was partially inhibited and distribution modified by infection.

Nakamura, T.; Fukagawa, S.; Kiryu, K., 1987: Fibroleiomyoma on a sow ear. Nihon Juigaku Zasshi. Japanese Journal of Veterinary Science 49(6): 1177-1179

Nishiyama, S.; Itoh, N.; Onosaka, S.; Okudaira, M.; Yamamoto, H.; Tanaka, K., 2003: Dietary cadmium inhibits spontaneous hepatocarcinogenesis in C3H/HeN mice and hepatitis in A/J mice, but not in C57BL/6 mice. Cadmium is known to be a potent carcinogenic and mutagenic metal. However, we demonstrated that dietary supplementation with 50 ppm cadmium inhibits spontaneous carcinogenesis in C3H/HeN and spontaneous hepatitis in A/J mice. We found that the fre...