Palladium catalyzed cross-coupling reactions for phosphorus-carbon bond formation

被引:285
作者
Schwan, AL [1 ]
机构
[1] Univ Guelph, Dept Chem & Biochem, Guelph, ON N1G 2W1, Canada
关键词
D O I
10.1039/b307538a
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Underappreciated in the realm of palladium catalyzed cross-coupling chemistry is the formation of phosphorous-carbon bonds. This tutorial review summarises a collection of important contributions in the area, providing a flavour of the many types of phosphorus species that are participants in palladium catalyzed phosphorus-carbon bond formation. Recent developments include the usage of the cross-coupling reaction for preparation of phosphine ligands and the involvement of low molecular weight phosphinic acid derivatives for the synthesis of unsaturated phosphinic and phosphonic acid derivatives. Mechanistic cycles are offered in some instances. Stereochemical issues are addressed where applicable. The literature is covered to mid 2003.
引用
收藏
页码:218 / 224
页数:7
相关论文
共 44 条
[1]   Commercially available 5′-DMT phosphoramidites as reagents for the synthesis of vinylphosphonate-linked oligonucleic acids [J].
Abbas, S ;
Bertram, RD ;
Hayes, CJ .
ORGANIC LETTERS, 2001, 3 (21) :3365-3367
[2]   A new synthetic route to P-chiral phosphine-boranes of high enantiopurity via stereocontrolled Pd(0)-Cu(I) cocatalyzed aromatic phosphorylation [J].
Al-Masum, M ;
Kumaraswamy, G ;
Livinghouse, T .
JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (15) :4776-4778
[3]   Catalytic methods for building up phosphorus-carbon bond [J].
Beletskaya, IP ;
Kazankova, MA .
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2002, 38 (10) :1391-1430
[4]   Pd-catalyzed synthesis of a tethered soluble polymeric phosphine ligand [J].
Bergbreiter, DE ;
Liu, YS ;
Furyk, S ;
Case, BL .
TETRAHEDRON LETTERS, 1998, 39 (48) :8799-8802
[5]   Water soluble phosphines - Part XV. Syntheses of multiply functionalized and chiral phosphine ligands by Pd-catalyzed P-C and C-C coupling reactions [J].
Brauer, DJ ;
Hingst, M ;
Kottsieper, KW ;
Liek, C ;
Nickel, T ;
Tepper, M ;
Stelzer, O ;
Sheldrick, WS .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2002, 645 (1-2) :14-26
[6]   Atropo-enantioselective synthesis of an axially chiral C1-symmetric phosphine ligand and its application in the asymmetric hydrosilylation of styrenes [J].
Bringmann, G ;
Wuzik, A ;
Breuning, M ;
Henschel, P ;
Peters, K ;
Peters, EM .
TETRAHEDRON-ASYMMETRY, 1999, 10 (15) :3025-3031
[7]   SYNTHESIS OF CHIRAL 2,2'-BIS(DIPHENYLPHOSPHINO)-1,1'-BINAPHTHYL (BINAP) VIA A NOVEL NICKEL-CATALYZED PHOSPHINE INSERTION [J].
CAI, DW ;
PAYACK, JF ;
BENDER, DR ;
HUGHES, DL ;
VERHOEVEN, TR ;
REIDER, PJ .
JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (23) :7180-7181
[8]  
Cai DW, 1999, ORG SYNTH, V76, P6
[9]  
Diederich F., 1998, METAL CATALYZED CROS, DOI DOI 10.1002/9783527612222
[10]   Synthesis of 1'-(2-(diarylphosphino)1-naphthyl)isoquinolines; variation of the aryl substituent [J].
Doucet, H ;
Brown, JM .
TETRAHEDRON-ASYMMETRY, 1997, 8 (22) :3775-3784