Catalyst Leaching as an Efficient Tool for Constructing New Catalytic Reactions: Application to the Synthesis of Cyclic Vinyl Sulfides and Vinyl Selenides

被引:37
作者
Ananikov, Valentine P. [1 ]
Gayduk, Konstantin A. [1 ]
Beletskaya, Irina P. [2 ]
Khrustalev, Victor N. [3 ]
Antipin, Mikhail Yu. [3 ]
机构
[1] Russian Acad Sci, Zelinsky Inst Organ Chem, Moscow 119991, Russia
[2] Moscow MV Lomonosov State Univ, Dept Chem, Moscow 119899, Russia
[3] Russian Acad Sci, AN Nesmeyanov Organoelement Cpds Inst, Moscow 119991, Russia
基金
俄罗斯基础研究基金会;
关键词
Homogeneous catalysis; Leaching; Nickel; Palladium; Nanoparticles; NUCLEAR MAGNETIC-RESONANCE; TRANSITION-METAL-COMPLEXES; SOLVENT-FREE CONDITIONS; SE BOND ADDITION; LIPOIC ACID; HETEROGENEOUS CATALYSIS; ZEROVALENT PALLADIUM; PYRAMIDAL INVERSION; OXIDATIVE ADDITION; CRYSTAL-STRUCTURE;
D O I
10.1002/ejic.200800984
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
Catalyst leaching from Pd and Ni particles stabilized by organic sulfur and selenium ligands occurs in solution in the presence of phosphanes. This process has been monitored in real time by 1D and 2D NMR spectroscopy and the nature of the metal species established. This catalyst leaching is shown to be a powerful tool for generating new catalytic activity from species formed in situ where the parent bulk particles are inactive. The catalytic system developed has been successfully implemented in a novel synthetic procedure that provides new types of cyclic sulfur and selenium compounds in high yields through the reaction between alkynes and dichalcogenides. ((C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)
引用
收藏
页码:1149 / 1161
页数:13
相关论文
共 73 条
[1]   DYNAMIC NUCLEAR MAGNETIC-RESONANCE STUDY OF GROUP-6 METAL PENTACARBONYL COMPLEXES - PYRAMIDAL INVERSION AND 1,2-METAL SHIFTS IN THE COMPLEXES [M(CO)5(ME2CCH2EECH2)] (M = CR, MO, OR W - E = S OR SE) [J].
ABEL, EW ;
MITTAL, PK ;
ORRELL, KG ;
SIK, V .
JOURNAL OF THE CHEMICAL SOCIETY-DALTON TRANSACTIONS, 1985, (08) :1569-1575
[2]   SYNTHESIS AND CRYSTAL-STRUCTURE OF [RE2CL2(CO)6(SECH2CME2CH2SE)] [J].
ABEL, EW ;
MITTAL, PK ;
ORRELL, KG ;
DAWES, H ;
HURSTHOUSE, MB .
POLYHEDRON, 1987, 6 (12) :2073-2075
[3]   SYNCHRONOUS PYRAMIDAL INVERSION OF CHALCOGEN ATOM PAIRS IN TRIMETHYLPLATINUM(IV) HALIDE-COMPLEXES WITH DITHIA-CYCLOPENTANE AND DISELENA-CYCLOPENTANE - X-RAY CRYSTAL-STRUCTURE OF [(PTIME3)2(ME2CCH2SESECH2)] [J].
ABEL, EW ;
MITTAL, PK ;
ORRELL, KG ;
SIK, V ;
CAMERON, TS .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1984, (19) :1312-1313
[4]   Oxidation of thiols to disulfides with molecular bromine on hydrated silica gel support [J].
Ali, MH ;
McDermott, M .
TETRAHEDRON LETTERS, 2002, 43 (35) :6271-6273
[5]   Remarkable ligand effect in Ni- and Pd-catalyzed bisthiolation and bisselenation of terminal alkynes:: Solving the problem of stereoselective dialkyldichalcogenide addition to the CC bond [J].
Ananikov, Valentine P. ;
Gayduk, Konstantin A. ;
Beletskaya, Irina P. ;
Khrustalev, Victor N. ;
Antipin, Mikhail Yu. .
CHEMISTRY-A EUROPEAN JOURNAL, 2008, 14 (08) :2420-2434
[6]   New approach for size- and shape-controlled preparation of pd nanoparticles with organic ligands. Synthesis and application in catalysis [J].
Ananikov, Valentine P. ;
Orlov, Nikolay V. ;
Beletskaya, Irina P. ;
Khrustalev, Victor N. ;
Antipin, Mikhail Yu. ;
Timofeeva, Tatiana V. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (23) :7252-+
[7]   Highly efficient nickel-based heterogeneous catalytic system with nanosized structural organization for selective Se-H bond addition to terminal and internal alkynes [J].
Ananikov, Valentine P. ;
Orlov, Nikolay V. ;
Beletskaya, Irina P. .
ORGANOMETALLICS, 2007, 26 (03) :740-750
[8]   Efficient and convenient synthesis of β-vinyl sulfides in nickel-catalyzed regioselective addition of thiols to terminal alkynes under solvent-free conditions [J].
Ananikov, VP ;
Orlov, NV ;
Beletskaya, IP .
ORGANOMETALLICS, 2006, 25 (08) :1970-1977
[9]   Palladium-catalyzed activation of E-E and C-E bonds in diaryl dichalcogenides (E = S, Se) under microwave irradiation conditions [J].
Ananikov, VP ;
Orlov, NV ;
Beletskaya, IP .
RUSSIAN CHEMICAL BULLETIN, 2005, 54 (03) :576-587
[10]   New catalytic system for S-S and Se-Se bond addition to alkynes based on phosphite ligands [J].
Ananikov, VP ;
Kabeshov, MA ;
Beletskaya, IP ;
Khrustalev, VN ;
Antipin, MY .
ORGANOMETALLICS, 2005, 24 (06) :1275-1283