Palladium-catalysed coupling of vinyl phosphates with aryl or heteroaryl boronic acids. Application to the synthesis of substituted nitrogen containing heterocycles

被引：42

作者：

Lepifre, F ^{[1
]}

Buon, C ^{[1
]}

Rabot, R ^{[1
]}

Bouyssou, P ^{[1
]}

Coudert, G ^{[1
]}

机构：

[1] Univ Orleans, CNRS, Inst Chim Organ & Analyt, F-45067 Orleans 02, France

来源：

TETRAHEDRON LETTERS | 1999年 / 40卷 / 35期

关键词：

coupling reactions; palladium; palladium compounds; boronic acids; benzoxazines; benzothiazines;

D O I：

10.1016/S0040-4039(99)01160-0

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Unusual substituted nitrogen-containing heterocycles were prepared in three steps from commercially available derivatives via an extension of the Suzuki reaction involving the palladium-catalysed coupling of vinyl phosphate with aryl or heteroarylboronic acids. (C) 1999 Published by Elsevier Science Ltd. All rights reserved.

引用

页码：6373 / 6376

页数：4

共 13 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] PYRIDINE-DERIVED TRIFLATING REAGENTS - AN IMPROVED PREPARATION OF VINYL TRIFLATES FROM METALLO ENOLATES [J].

COMINS, DL ;

DEHGHANI, A .

TETRAHEDRON LETTERS, 1992, 33 (42) :6299-6302

[3] SYNTHESIS AND NMR-SPECTRA OF THE 6 ISOMERIC THIENO[C]-FUSED 1,7-NAPHTHYRIDINES AND 1,8-NAPHTHYRIDINES [J].

MALM, J ;

REHN, B ;

HORNFELDT, AB ;

GRONOWITZ, S .

JOURNAL OF HETEROCYCLIC CHEMISTRY, 1994, 31 (01) :11-15

[4] A METHOD FOR THE REGIOSPECIFIC SYNTHESIS OF ENOL TRIFLATES BY ENOLATE TRAPPING [J].

MCMURRY, JE ;

SCOTT, WJ .

TETRAHEDRON LETTERS, 1983, 24 (10) :979-982

[5] THE PALLADIUM-CATALYZED CROSS-COUPLING REACTION OF PHENYLBORONIC ACID WITH HALOARENES IN THE PRESENCE OF BASES [J].

MIYAURA, N ;

YANAGI, T ;

SUZUKI, A .

SYNTHETIC COMMUNICATIONS, 1981, 11 (07) :513-519

[6]

MOENOMANAS M, 1995, J ORG CHEM, V60, P2396

[7] Palladium-catalyzed functionalization of lactones via their cyclic ketene acetal phosphates. Efficient new synthetic technology for the construction of medium and large cyclic ethers [J].

Nicolaou, KC ;

Shi, GQ ;

Gunzner, JL ;

Gartner, P ;

Yang, Z .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (23) :5467-5468

[8]

STANG PJ, 1982, SYNTHESIS-STUTTGART, P85

[9] PREPARATION AND SOLVOLYSIS OF VINYL TRIFLUOROMETHANESULFONATES .I. EVIDENCE FOR SIMPLE ALKYLVINYL CATION INTERMEDIATES [J].

STANG, PJ ;

SUMMERVI.R .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1969, 91 (16) :4600-&

[10]

SURI SC, 1990, SYNTHESIS-STUTTGART, P695

← 1 2 →