Performance of chiral tetracarbonylmolybdenum pyrindanyl amine complexes in catalytic olefin epoxidation

被引：8
作者：
Neves, Patricia [1 ]
Nogueira, Lucie S. [1 ]
Valente, Anabela A. [1 ]
Pillinger, Martyn [1 ]
Goncalves, Isabel S. [1 ]
Sampaio-Dias, Ivo E. [2 ]
Sousa, Carlos A. D. [2 ]
Rizzo-Aguiar, Fabio [3 ]
Rodriguez-Borges, Jose E. [2 ]
机构：
[1] Univ Aveiro, CICECO Aveiro Inst Mat, Dept Chem, Campus Univ Santiago, P-3810193 Aveiro, Portugal
[2] Univ Porto, Fac Sci, Dept Chem & Biochem, LAQV REQUIMTE, P-4169007 Oporto, Portugal
[3] IFSP Fed Inst Educ Sci & Technol Sao Paulo, Campus Sao Paulo, BR-01109010 Sao Paulo, SP, Brazil
来源：
JOURNAL OF ORGANOMETALLIC CHEMISTRY | 2018年 / 858卷
关键词：
Molybdenum; Tetracarbonyl complexes; Olefin epoxidation; Chiral ligands; 1-pyrindane derivatives; Oxidative decarbonylation; ALTERNATING COPOLYMERIZATION; HYDROGEN-PEROXIDE; HYBRID MATERIALS; MOLYBDENUM; LIMONENE; OCTAMOLYBDATE; CARBONYL; PRECURSORS; ALCOHOL; ROUTE;
D O I：
10.1016/j.jorganchem.2018.01.003
中图分类号：
O61 [无机化学];
学科分类号：
070301 ; 081704 ;
摘要：
Tetracarbonylmolybdenum(0) complexes of the type cis-[Mo(CO)(4)(L)] containing chiral 7-(1-pyrindanyl) amine ligands were prepared and found to be effective precatalysts for the epoxidation of achiral (cis-cyclooctene) and prochiral (DL-limonene and trans-beta-methylstyrene) olefins at 55 degrees C. Epoxides were the only products formed from cis-cyclooctene (100% yield) and trans-b-methylstyrene (100% selectivity at 82-85% conversion), and the main products formed from DL-limonene (80-82% 1,2-epoxide selectivity at 85% conversion). Characterization of recovered catalysts revealed that the precatalysts were transformed in situ to stable polyoxomolybdate salts containing the beta-octamolybdate anion [beta-Mo8O26](4-), which was responsible for the catalytic reaction. (c) 2018 Elsevier B.V. All rights reserved.
引用
收藏
页码：29 / 36
页数：8
相关论文
共 57 条
[1]   A simple entry to (η5-C5R5)chlorodioxomolybdenum(VI) complexes (R = H, CH3, CH2Ph) and their use as olefin epoxidation catalysts [J].
Abrantes, M ;
Santos, AM ;
Mink, J ;
Kühn, FE ;
Romao, CC .
ORGANOMETALLICS, 2003, 22 (10) :2112-2118
[2]   Characterization of a chiral menthyldimethyltin molybdate and its use as an olefin epoxidation catalyst [J].
Abrantes, Marta ;
Valente, Anabela A. ;
Pillinger, Martyn ;
Romao, Carlos C. ;
Goncalves, Isabel S. .
CATALYSIS LETTERS, 2007, 114 (1-2) :103-109
[3]   A chiral menthyl cyclopentadienyl molybdenum tricarbonyl chloro complex:: Synthesis, heterogenization on MCM-41/MCM-48 and application in olefin epoxidation catalysis [J].
Abrantes, Marta ;
Sakthivel, Ayyamperumal ;
Romao, Carlos C. ;
Kuehn, Fritz E. .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2006, 691 (14) :3137-3145
[4]   Amino acid-functionalized cyclopentadienyl molybdenum tricarbonyl complex and its use in catalytic olefin epoxidation [J].
Abrantes, Marta ;
Paz, Filipe A. Almeida ;
Valente, Anabela A. ;
Pereira, Claudia C. L. ;
Gago, Sandra ;
Rodrigues, Alirio E. ;
Klinowski, Jacek ;
Pillinger, Martyn ;
Goncalves, Isabel S. .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2009, 694 (12) :1826-1833
[5]   Investigation of Molybdenum Tetracarbonyl Complexes As Precursors to MoVI Catalysts for the Epoxidation of Olefins [J].
Amarante, Tatiana R. ;
Neves, Patricia ;
Coelho, Ana C. ;
Gago, Sandra ;
Valente, Anabela A. ;
Paz, Filipe A. Almeida ;
Pillinger, Martyn ;
Goncalves, Isabel S. .
ORGANOMETALLICS, 2010, 29 (04) :883-892
[6]   Cyclic limonene dicarbonate as a new monomer for non-isocyanate oligo- and polyurethanes (NIPU) based upon terpenes [J].
Baehr, Moritz ;
Bitto, Alexandro ;
Muelhaupt, Rolf .
GREEN CHEMISTRY, 2012, 14 (05) :1447-1454
[7]   An environmentally friendly route for grafting of molybdenum carbonyl onto a diaminosilane-modified SBA-15 molecular sieve and its catalytic behaviour in olefin epoxidation [J].
Baskaran, Thangaraj ;
Kumaravel, Raju ;
Christopher, Jayaraj ;
Ajithkumar, Thalasseril G. ;
Sakthivel, Ayyamperumal .
NEW JOURNAL OF CHEMISTRY, 2015, 39 (05) :3758-3764
[8]  
Bregeault J.-M., 2003, J CHEM SOC DA, P3289
[9]   Molybdenum-catalysed oxidation of cyclohexene with hydrogen peroxide in the presence of alcohols and X-ray structures of octamolybdate [C4mim]4[Mo8O26] and tetraperoxodimolybdate [Htmpy]2[{MoO(O2)2}2(μ-O)] complexes [J].
Carrasco, Carlos J. ;
Montilla, Francisco ;
Alvarez, Eleuterio ;
Herbert, Matthew ;
Galindo, Agustin .
POLYHEDRON, 2013, 54 :123-130
[10]   Perillyl Alcohol for the Treatment of Temozolomide-Resistant Gliomas [J].
Cho, Hee-Yeon ;
Wang, Weijun ;
Jhaveri, Niyati ;
Torres, Shering ;
Tseng, Joshua ;
Leong, Michelle N. ;
Lee, David Jungpa ;
Goldkorn, Amir ;
Xu, Tong ;
Petasis, Nicos A. ;
Louie, Stan G. ;
Schoenthal, Axel H. ;
Hofman, Florence M. ;
Chen, Thomas C. .
MOLECULAR CANCER THERAPEUTICS, 2012, 11 (11) :2462-2472
123456