Alkyne and Alkene Insertion into Metal-Heteroatom and Metal-Hydrogen Bonds: The Key Stages of Hydrofunctionalization Process

被引:115
作者
Ananikov, Valentine P. [1 ]
Beletskaya, Irina P. [2 ]
机构
[1] Russian Acad Sci, Zelinsky Inst Organ Chem, Moscow 119991, Russia
[2] Moscow MV Lomonosov State Univ, Dept Chem, Moscow 119899, Russia
来源
HYDROFUNCTIONALIZATION | 2013年 / 43卷
关键词
Alkenes; Alkynes; Catalysis Insertion Mechanism; Selectivity; CARBON-CARBON; C-C; N BOND; PALLADIUM; VINYL; PD; ACTIVATION; COMPLEXES; HYDROTHIOLATION; REACTIVITY;
D O I
10.1007/3418_2012_54
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
In this chapter we review mechanistic concepts of carbon-heteroatom bond formation involving hydrofunctionalization of double and triple carbon carbon bonds via migratory insertion pathway. A variety of useful synthetic procedures were developed within the scope of hydrofunctionalization reaction involving transition metal catalysts to change the direction of the addition reaction and to improve the selectivity of the process. Outstanding potential of multiple bonds activation and insertion in the metal complexes is far from being fully explored. The key factors determining insertion pathways into metal-heteroatom vs. metal hydrogen bonds and the influence on regioselectivity of the insertion remain to be revealed in nearest future.
引用
收藏
页码:1 / 19
页数:19
相关论文
共 54 条
[11]   Two Distinct Mechanisms of Alkyne Insertion into the Metal-Sulfur Bond: Combined Experimental and Theoretical Study and Application in Catalysis [J].
Ananikov, Valentine P. ;
Gayduk, Konstantin A. ;
Orlov, Nikolay V. ;
Beletskaya, Irina P. ;
Khrustalev, Victor N. ;
Antipin, Mikhail Yu. .
CHEMISTRY-A EUROPEAN JOURNAL, 2010, 16 (07) :2063-2071
[12]   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
[13]   Theoretical insight into the C-C coupling reactions of the vinyl, phenyl, ethynyl, and methyl complexes of palladium and platinum [J].
Ananikov, VP ;
Musaev, DG ;
Morokuma, K .
ORGANOMETALLICS, 2005, 24 (04) :715-723
[14]   Catalytic triple bond activation and vinyl-vinyl reductive coupling by Pt(IV) complexes. A density functional study [J].
Ananikov, VP ;
Musaev, DG ;
Morokuma, K .
ORGANOMETALLICS, 2001, 20 (08) :1652-1667
[15]  
[Anonymous], 2009, ORGANOTRANSITION MET
[16]   Binding energy of d10 transition metals to alkenes by wave function theory and density functional theory [J].
Averkiev, Boris B. ;
Zhao, Yan ;
Truhlar, Donald G. .
JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2010, 324 (1-2) :80-88
[17]   C-C, C-O, C-N bond formation on sp2 carbon by Pd(II)-catalyzed reactions involving oxidant agents [J].
Beccalli, Egle M. ;
Broggini, Gianluigi ;
Martinelli, Michela ;
Sottocornola, Silvia .
CHEMICAL REVIEWS, 2007, 107 (11) :5318-5365
[18]   Element-element additions to unsaturated carbon-carbon bonds catalyzed by transition metal complexes [J].
Beletskaya, Irina ;
Moberg, Christina .
CHEMICAL REVIEWS, 2006, 106 (06) :2320-2354
[19]   Transition-Metal-Catalyzed C-S, C-Se, and C-Te Bond Formation via Cross-Coupling and Atom-Economic Addition Reactions [J].
Beletskaya, Irina P. ;
Ananikov, Valentine P. .
CHEMICAL REVIEWS, 2011, 111 (03) :1596-1636
[20]   Organometallic Approaches to Carbon-Sulfur Bond Formation [J].
Bichler, Paul ;
Love, Jennifer A. .
C-X BOND FORMATION, 2010, 31 :39-64