A general method to prepare monodentate phosphane ligands with mixed substituents
作者： Jennifer E. Phelps , Sara B. Frawley , R. Gregory Peters
DOI: 10.1002/HC.20563
关键词: Denticity 、 Medicinal chemistry 、 Protecting group 、 Chemistry 、 Ring (chemistry) 、 Heteroatom 、 Reagent 、 Substituent 、 Stereochemistry 、 Alkyl 、 General method
摘要: Treatment of (2,2′-biphenylylene)- phosphorchloridite ester [(C12H8O2)PCl] (1) with C2F5Li yields (C12H8O2)PC2F52; treatment 1 Grignard reagents compounds the type (C12H8O2)PR (R = iPr, 5; Et 6). In both cases, 1,3-dioxepine ring formed when 2,2′-biphenol reacts PCl3 to form serves as a protecting group at phosphorus atom; allows stepwise introduction one substituent and prevents undesirable product mixtures associated multiple substitutions phosphorus. Additional 2, 5, 6 Grignard, alkyl-, or aryllithium results in formation unsymmetrically substituted phosphanes. The use (2,2′-biphenylylene)phosphorchloridite starting material for preparation electroneutral phosphanes (Rf)PR2 electron-poor (Rf)2PR is described. © 2010 Wiley Periodicals, Inc. Heteroatom Chem 20:393–397, 2009; Published online InterScience (www.interscience.wiley.com). DOI 10.1002/hc.20563
sci-hub.se 参考文章(17)
Donald J. Burton, Zhen-Yu Yang, Peter A. Morken, Fluorinated organometallics: Vinyl, alkynyl, allyl, benzyl, propargyl and aryl : Fluorinated organometallic reagents in organic synthesis Tetrahedron. ,vol. 50, pp. 2993- 3063 ,(1994) , 10.1016/S0040-4020(01)81105-4
M. Fild, O. Stelzer, R. Schmutzler, G. O. Doak, Tert‐butyldichlorophosphine and Di‐tert‐butylchlorophosphine John Wiley & Sons, Ltd. pp. 4- 9 ,(2007) , 10.1002/9780470132456.CH2
Kulbinder K. Banger, Russell P. Banham, Alan K. Brisdon, Wendy I. Cross, Greame Damant, Simon Parsons, Robin G. Pritchard, Antonio Sousa-Pedrares, Synthesis and co-ordination chemistry of perfluorovinyl phosphine derivatives. Single crystal structures of PPh(CFCF2)2, cis-[PtCl2{PPh2(CFCF2)}2] and [{AuCl[PPh2(CFCF2)]}2] Journal of The Chemical Society-dalton Transactions. pp. 427- 434 ,(1999) , 10.1039/A806535G
Houston Byrd, Jeremiah D. Harden, Jennifer M. Butler, Michael J. Jablonsky, Gary M. Gray, Nucleophilic displacement reactions of cis-bis((2,2'-biphenylylene)phosphochloridite ester)tetracarbonylmolybdenum(0). The first example of an unusual hydrolysis reaction yielding unsymmetrically substituted products Organometallics. ,vol. 22, pp. 4198- 4205 ,(2003) , 10.1021/OM030411Z
N.A Barnes, A.K Brisdon, M.J Ellis, R.G Pritchard, Recent advances in fluorovinyl-containing compounds Journal of Fluorine Chemistry. ,vol. 112, pp. 35- 45 ,(2001) , 10.1016/S0022-1139(01)00479-1
Kulbinder K. Banger, Alan K. Brisdon, Arti Gupta, Perfluorovinyl–metal derivatives: a new one-pot synthesis Chemical Communications. pp. 139- 140 ,(1997) , 10.1039/A605732B
R. Gregory Peters, Byron L. Bennett, R. Chris Schnabel, Dean M. Roddick, (Fluoroalkyl)phosphine Coordination Chemistry: Synthesis and Structure of {[m,eta(1),eta(6)-(C(6)H(5))P(C(2)F(5))(2)]Cr(CO)(2)}(2). Inorganic Chemistry. ,vol. 36, pp. 5962- 5965 ,(1997) , 10.1021/IC970672Z
Franck Rataboul, Alexander Zapf, Ralf Jackstell, Surendra Harkal, Thomas Riermeier, Axel Monsees, Uwe Dingerdissen, Matthias Beller, New ligands for a general palladium-catalyzed amination of aryl and heteroaryl chlorides. Chemistry: A European Journal. ,vol. 10, pp. 2983- 2990 ,(2004) , 10.1002/CHEM.200306026
Jason D. Palcic, P. N. Kapoor, Dean M. Roddick, R. Gregory Peters, Perfluoroalkylphosphine coordination chemistry of platinum: synthesis of (C2F5)2PPh and (C2F5)PPh2 complexes of platinum(II) Dalton Transactions. pp. 1644- 1647 ,(2004) , 10.1039/B400995A
Katharine D. Cooney, Thomas R. Cundari, Norris W. Hoffman, Karl A. Pittard, M. Danielle Temple, Yong Zhao, A Priori Assessment of the Stereoelectronic Profile of Phosphines and Phosphites Journal of the American Chemical Society. ,vol. 125, pp. 4318- 4324 ,(2003) , 10.1021/JA021254I