Efficient method for the synthesis of diphosphine ligands with a heteroaryl-aryl bridge

被引:13
作者
Artemova, NV
Chevykalova, MN
Luzikov, YN
Nifant'ev, IE [1 ]
Nifant'ev, EE
机构
[1] Moscow MV Lomonosov State Univ, Dept Chem, Moscow 119992, Russia
[2] Moscow State Pedag Univ, Dept Chem, Moscow 119021, Russia
关键词
heterocycles; phosphorylation; diphosphines; indole; thiophene;
D O I
10.1016/j.tet.2004.07.082
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A new efficient method for the synthesis of heteroaryl-aryl diphosphine ligands by direct double metallation of heteroaryl-aryls followed by phosphorylation of the resulting o,o'-dilithium salts is described. A number of new C-1-symmetric diphosphine ligands based on 3-arylheteroaryls, X-heteroaryls (X=N), and diphosphine ligands with a heterocyclic bridge with o-tolyl as the aryl fragment have been synthesized. (C) 2004 Elsevier Ltd. All rights reserved.
引用
收藏
页码:10365 / 10370
页数:6
相关论文
共 29 条
[1]   3,3′-bis(diphenylphosphino)-1,1′-disubstituted-2,2′-biindoles:: Easily accessible, electron-rich, chiral diphosphine ligands for homogeneous enantioselective hydrogenation of oxoesters [J].
Benincori, T ;
Piccolo, O ;
Rizzo, S ;
Sannicolò, F .
JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (24) :8340-8347
[2]   2,2′,5,5′-tetramethyl-4,4′-bis(diphenylphoshino)-3,3′-bithiophene:: A new, very efficient, easily accessible, chiral biheteroaromatic ligand for homogeneous stereoselective catalysis [J].
Benincori, T ;
Cesarotti, E ;
Piccolo, O ;
Sannicolò, F .
JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (07) :2043-2047
[3]   A new modular class of easily accessible, inexpensive, and efficient chiral diphosphine ligands for homogeneous stereoselective catalysis [J].
Benincori, T ;
Gladiali, S ;
Rizzo, S ;
Sannicolò, F .
JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (17) :5940-5942
[4]   New class of chiral diphosphine ligands for highly efficient transition metal-catalyzed stereoselective reactions: The bis(diphenylphosphino) five-membered biheteroaryls [J].
Benincori, T ;
Brenna, E ;
Sannicolo, F ;
Trimarco, L ;
Antognazza, P ;
Cesarotti, E ;
Demartin, F ;
Pilati, T .
JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (18) :6244-6251
[5]   SYNTHESIS OF 3-SUBSTITUTED INDOLES STARTING FROM ISATIN [J].
BERGMAN, J .
ACTA CHEMICA SCANDINAVICA, 1971, 25 (04) :1277-&
[6]  
Brunner H, 1993, HDB ENANTIOSELECTIVE, V2
[7]   (R)- and (S)-6,6'-dimethyl- and 6,6'-dimethoxy-2,2'-diiodo-1,1'-biphenyls: Versatile intermediates for the synthesis of atropisomeric diphosphine ligands [J].
Cereghetti, M ;
Arnold, W ;
Broger, EA ;
Rageot, A .
TETRAHEDRON LETTERS, 1996, 37 (30) :5347-5350
[8]   CYCLODEHYDRATION PROCESSES .1. BENZOFURAN DERIVATIVES FORMED BY CYCLISATION OF OMEGA-ARYLOXYACETOPHENONES [J].
DAVIES, W ;
MIDDLETON, S .
JOURNAL OF THE CHEMICAL SOCIETY, 1958, (FEB) :822-825
[9]  
Franciò G, 2000, ANGEW CHEM INT EDIT, V39, P1428, DOI 10.1002/(SICI)1521-3773(20000417)39:8<1428::AID-ANIE1428>3.0.CO
[10]  
2-K