Regiospecific Calcium-Mediated Intermolecular Hydrophosphanylation of Butadiynes with Diphenylphosphane Oxide

被引:14
作者
Al-Shboul, Tareq M. A. [1 ]
Goerls, Helmar [1 ]
Krieck, Sven [1 ]
Westerhausen, Matthias [1 ]
机构
[1] Univ Jena, Inst Anorgan & Analyt Chem, D-07743 Jena, Germany
关键词
Calcium; Phosphorus; Alkynes; Regioselectivity; CARBON BOND FORMATION; CRYSTAL-STRUCTURE; TRIPHENYLPHOSPHINE OXIDE; ASYMMETRIC-SYNTHESIS; COMPLEXES; HYDROPHOSPHINATION; CATALYSIS; STRONTIUM; BARIUM; DERIVATIVES;
D O I
10.1002/ejic.201201138
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
Calcium-mediated hydrophosphanylation of diphenyl- and di(tert-butyl)butadiyne (2,2,7,7-tetramethyl-3,5-octadiyne) with diphenylphosphane oxide yields 1,4-diphenyl-1,3-butadiene-2,3-bis(diphenylphosphane oxide) and 2,2,7,7-tetramethyl-4-octyne-3,6-bis(diphenylphosphane oxide), respectively. Alternatively, 1,4-diphenylphosphanyl-substituted 1,4-butadienes are quantitatively oxidized by H2O2 to the corresponding 1,3-butadiene-1,4-bis(diphenylphosphane oxides).
引用
收藏
页码:5451 / 5455
页数:5
相关论文
共 43 条
[1]   Oxidation Products of Calcium and Strontium Bis(diphenylphosphanide) [J].
Al-Shboul, Tareq M. A. ;
Volland, Gritt ;
Goerls, Helmar ;
Krieck, Sven ;
Westerhausen, Matthias .
INORGANIC CHEMISTRY, 2012, 51 (14) :7903-7912
[2]   Catalytic synthesis of vinylphosphanes via calcium-mediated intermolecular hydrophosphanylation of alkynes and butadiynes [J].
Al-Shboul, Tareq M. A. ;
Palfi, Villoe K. ;
Yu, Lian ;
Kretschmer, Robert ;
Wimmer, Katja ;
Fischer, Reinald ;
Goerls, Helmar ;
Reiher, Markus ;
Westerhausen, Matthias .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2011, 696 (01) :216-227
[3]   Calcium-mediated hydrophosphination of diphenylethyne and diphenylbutadiyne as well as crystal structure of 1,4-diphenyl-1,4-bis(diphenylphosphanyl)buta-1,3-diene [J].
Al-Shboul, Tareq M. A. ;
Goerls, Helmar ;
Westerhausen, Matthias .
INORGANIC CHEMISTRY COMMUNICATIONS, 2008, 11 (12) :1419-1421
[4]   Organocatalytic Asymmetric Synthesis of Organophosphorus Compounds [J].
Albrecht, Lukasz ;
Albrecht, Anna ;
Krawczyk, Henryk ;
Jorgensen, Karl Anker .
CHEMISTRY-A EUROPEAN JOURNAL, 2010, 16 (01) :28-48
[5]   Catalytic Hydrofunctionalization of Alkynes through P-H Bond Addition: The Unique Role of Orientation and Properties of the Phosphorus Group in the Insertion Step [J].
Ananikov, Valentine P. ;
Makarov, Anton V. ;
Beletskaya, Irina P. .
CHEMISTRY-A EUROPEAN JOURNAL, 2011, 17 (45) :12623-12630
[6]  
[Anonymous], 1998, COLLECT DATA COLLECT
[7]  
[Anonymous], ANGEW CHEM
[8]   Catalytic synthesis of phosphines and related compounds [J].
Baillie, C ;
Xiao, JL .
CURRENT ORGANIC CHEMISTRY, 2003, 7 (05) :477-514
[9]   Synthesis, characterization, and solution lability of N-heterocyclic carbene adducts of the heavier group 2 bis(trimethylsilyl)amides [J].
Barrett, Anthony G. M. ;
Crimmin, Mark R. ;
Hill, Michael S. ;
Kociok-Koehn, Gabriele ;
MacDougall, Dugald J. ;
Mahon, Mary F. ;
Procopiou, Panayiotis A. .
ORGANOMETALLICS, 2008, 27 (15) :3939-3946
[10]   Heterofunctionalization catalysis with organometallic complexes of calcium, strontium and barium [J].
Barrett, Anthony G. M. ;
Crimmin, Mark R. ;
Hill, Michael S. ;
Procopiou, Panayiotis A. .
PROCEEDINGS OF THE ROYAL SOCIETY A-MATHEMATICAL PHYSICAL AND ENGINEERING SCIENCES, 2010, 466 (2116) :927-963