Efficient, protection-free Suzuki-Miyaura synthesis of ortho-biphenyltetrazoles

被引:13
作者
Cousaert, N [1 ]
Toto, P [1 ]
Willand, N [1 ]
Deprez, B [1 ]
机构
[1] Fac Sci Pharmaceut & Biol, UMR 8525, Lab Chim Gen & Chim Organ, F-59006 Lille, France
关键词
ortho-biphenyltetrazole; Suzuki-Miyaura cross-coupling; microwave synthesis;
D O I
10.1016/j.tetlet.2005.07.082
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
We describe an efficient protocol for the Suzuki-Miyaura synthesis of ortho-biphenyltetrazoles from non-protected 2-bromophenyltetrazole and arylboronic acids. The optimised conditions were achieved using [1, 1 '-bis(diphenylphosphino)ferrocene]dichloropalladium(II) as catalyst and Na2CO3 as base. A panel of structurally diverse arylboronic acids was used to demonstrate the scope of the coupling procedure. (c) 2005 Elsevier Ltd. All rights reserved.
引用
收藏
页码:6529 / 6532
页数:4
相关论文
共 14 条
[1]   SEQUENTIAL DIRECTED ORTHO METALATION BORONIC ACID CROSS-COUPLING REACTIONS - A GENERAL REGIOSPECIFIC ROUTE TO OXYGENATED DIBENZO[B,D]PYRAN-6-ONES RELATED TO ELLAGIC ACID [J].
ALO, BI ;
KANDIL, A ;
PATIL, PA ;
SHARP, MJ ;
SIDDIQUI, MA ;
SNIECKUS, V ;
JOSEPHY, PD .
JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (12) :3763-3768
[2]   ANGIOTENSIN RECEPTOR ANTAGONISTS - FOCUS ON LOSARTAN [J].
JOHNSTON, CI .
LANCET, 1995, 346 (8987) :1403-1407
[3]   A novel and expeditious route to A-81988: An angiotensin II receptor antagonist [J].
Kerdesky, FAJ ;
Sowin, TJ .
SYNTHETIC COMMUNICATIONS, 1996, 26 (05) :1007-1013
[4]   First synthesis and electronic properties of (hetero)aryl bridged and directly linked redox active phenothiazinyl dyads and triads [J].
Krämer, CS ;
Zeitler, K ;
Müller, TJJ .
TETRAHEDRON LETTERS, 2001, 42 (49) :8619-8624
[5]   EFFICIENT SYNTHESIS OF LOSARTAN, A NONPEPTIDE ANGIOTENSIN-II RECEPTOR ANTAGONIST [J].
LARSEN, RD ;
KING, AO ;
CHEN, CY ;
CORLEY, EG ;
FOSTER, BS ;
ROBERTS, FE ;
YANG, CH ;
LIEBERMAN, DR ;
REAMER, RA ;
TSCHAEN, DM ;
VERHOEVEN, TR ;
REIDER, PJ .
JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (21) :6391-6394
[6]   Acyclic structural variants of growth hormone secretagogue L-692,429 [J].
Lin, P ;
Pisano, JM ;
Schoen, WR ;
Cheng, K ;
Chan, WWS ;
Butler, BS ;
Smith, RG ;
Fisher, MH ;
Wyvratt, MJ .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1999, 9 (22) :3237-3242
[7]   ARYL COUPLINGS WITH HETEROGENEOUS PALLADIUM CATALYSTS [J].
MARCK, G ;
VILLIGER, A ;
BUCHECKER, R .
TETRAHEDRON LETTERS, 1994, 35 (20) :3277-3280
[8]   PALLADIUM-CATALYZED CROSS-COUPLING REACTIONS OF ORGANOBORON COMPOUNDS [J].
MIYAURA, N ;
SUZUKI, A .
CHEMICAL REVIEWS, 1995, 95 (07) :2457-2483
[9]   A general route to pyridine-modified salicylaldehydes via Suzuki coupling [J].
Morris, GA ;
Nguyen, SBT .
TETRAHEDRON LETTERS, 2001, 42 (11) :2093-2096
[10]   MECHANISTIC STUDIES OF THE SUZUKI CROSS-COUPLING REACTION [J].
SMITH, GB ;
DEZENY, GC ;
HUGHES, DL ;
KING, AO ;
VERHOEVEN, TR .
JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (26) :8151-8156