ADC-Based Palladium Catalysts for Aqueous Suzuki–Miyaura Cross-Coupling Exhibit Greater Activity than the Most Advantageous Catalytic Systems
3
Publication type: Journal Article
Publication date: 2013-09-04
scimago Q2
wos Q1
SJR: 0.676
CiteScore: 5.1
Impact factor: 2.9
ISSN: 02767333, 15206041
Organic Chemistry
Inorganic Chemistry
Physical and Theoretical Chemistry
Abstract
The reaction between the equimolar amounts of cis-[PdCl2(CNR1)2] (R1 = cyclohexyl (Cy) (1), tBu (2)) and the carbohydrazides R2CONHNH2 (R2 = Ph (5), 4-ClC6H4 (6), 3-NO2C6H4 (7), 4-NO2C6H4 (8), 4-CH3C6H4 (9), 3,4-(MeO)2C6H3 (10), naphth-1-yl (11), fur-2-yl (12), 4-NO2C6H4CH2 (13), Cy (14), 1-(4-fluorophenyl)-5-oxopyrrolidin-3-yl (15), (pyrrolidin-1-yl)C(O) (16)) proceeds in refluxing CHCl3 for ca. 4 h. A subsequent workup provided the aminocarbene species cis-[PdCl2{C(NHNHC(O)R2)═N(H)R1}(CNR1)] (18–33) in good to excellent (80–95%) isolated yields. The coupling of equimolar amounts of cis-[PdCl2(CNR1)2] (R1 = Cy (1), tBu (2), 2,6-Me2C6H3 (Xyl) (3), 2-Cl-6-MeC6H3 (4)) and PhSO2NHNH2 (17) occurs similarly and affords the aminocarbenes cis-[PdCl2{C(NHNHS(O)2Ph)═N(H)R1}(CNR1)] (34–37; 60–90%). Complexes 18–37 were characterized by elemental analyses (C, H, N), ESI+-MS, IR, and 1D (1H, 13C{1H}) and 2D (1H,1H-COSY, 1H,13C-HMQC/1H,13C-HSQC, 1H,13C-HMBC) NMR spectroscopy, as well as by X-ray diffraction for three ...
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Kinzhalov M. A. et al. ADC-Based Palladium Catalysts for Aqueous Suzuki–Miyaura Cross-Coupling Exhibit Greater Activity than the Most Advantageous Catalytic Systems // Organometallics. 2013. Vol. 32. No. 18. pp. 5212-5223.
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Kinzhalov M. A., Luzyanin K., Boyarskiy V. P., Haukka M., Kukushkin V. Y. ADC-Based Palladium Catalysts for Aqueous Suzuki–Miyaura Cross-Coupling Exhibit Greater Activity than the Most Advantageous Catalytic Systems // Organometallics. 2013. Vol. 32. No. 18. pp. 5212-5223.
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RIS
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TY - JOUR
DO - 10.1021/om4007592
UR - https://doi.org/10.1021/om4007592
TI - ADC-Based Palladium Catalysts for Aqueous Suzuki–Miyaura Cross-Coupling Exhibit Greater Activity than the Most Advantageous Catalytic Systems
T2 - Organometallics
AU - Kinzhalov, M. A.
AU - Luzyanin, Konstantin
AU - Boyarskiy, Vadim P
AU - Haukka, Matti
AU - Kukushkin, Vadim Yu.
PY - 2013
DA - 2013/09/04
PB - American Chemical Society (ACS)
SP - 5212-5223
IS - 18
VL - 32
SN - 0276-7333
SN - 1520-6041
ER -
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BibTex (up to 50 authors)
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@article{2013_Kinzhalov,
author = {M. A. Kinzhalov and Konstantin Luzyanin and Vadim P Boyarskiy and Matti Haukka and Vadim Yu. Kukushkin},
title = {ADC-Based Palladium Catalysts for Aqueous Suzuki–Miyaura Cross-Coupling Exhibit Greater Activity than the Most Advantageous Catalytic Systems},
journal = {Organometallics},
year = {2013},
volume = {32},
publisher = {American Chemical Society (ACS)},
month = {sep},
url = {https://doi.org/10.1021/om4007592},
number = {18},
pages = {5212--5223},
doi = {10.1021/om4007592}
}
Cite this
MLA
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Kinzhalov, M. A., et al. “ADC-Based Palladium Catalysts for Aqueous Suzuki–Miyaura Cross-Coupling Exhibit Greater Activity than the Most Advantageous Catalytic Systems.” Organometallics, vol. 32, no. 18, Sep. 2013, pp. 5212-5223. https://doi.org/10.1021/om4007592.
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