A 2-pyrone cycloaddition route to functionalised aromatic boronic esters

被引：43

作者：

Delaney, Patrick M. ^{[1
]}

Browne, Duncan L. ^{[1
]}

Adams, Harry ^{[1
]}

Plant, Andrew ^{[2
]}

Harrity, Joseph P. A. ^{[1
]}

机构：

[1] Univ Sheffield, Dept Chem, Sheffield S3 7HF, S Yorkshire, England

[2] Jealotts Hill Int Res Ctr, Bracknell RG42 6EY, Berks, England

来源：

TETRAHEDRON | 2008年 / 64卷 / 05期

基金：

英国工程与自然科学研究理事会;

关键词：

D O I：

10.1016/j.tet.2007.08.118

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A [4+2] cycloaddition/retro-cycloaddition route to functionalised aromatic boronic esters is outlined. A range of electron deficient dienes (2-pyrones) and dienophiles (alkynylboronates) were found to participate in the reaction. Furthermore, high levels of regiocontrol could be obtained in this process and a consistent mode of alkyne insertion has been uncovered. (c) 2007 Elsevier Ltd. All rights reserved.

引用

页码：866 / 873

页数：8

共 40 条

[1] An experimental and computational investigation of the Diels-Alder cycloadditions of halogen-substituted 2(H)-pyran-2-ones [J].

Afarinkia, K ;

Bearpark, MJ ;

Ndibwami, A .

JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (04) :1122-1133

[2] A new route for manufacture of 3-cyano-1-naphthalenecarboxylic acid [J].

Ashworth, IW ;

Bowden, MC ;

Dembofsky, B ;

Levin, D ;

Moss, W ;

Robinson, E ;

Szczur, N ;

Virica, J .

ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2003, 7 (01) :74-81

[3] 5-ISOXAZOLEBORONIC ACIDS [J].

BIANCHI, G ;

COGOLI, A ;

GRUNANCE.P .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1966, 6 (06) :598-&

[4]

Blanchard C, 1996, SYNTHESIS-STUTTGART, P45

[5] Mechanism of the mild functionalization of arenes by diboron reagents catalyzed by iridium complexes. Intermediacy and chemistry of bipyridine-ligated iridium trisboryl complexes [J].

Boller, TM ;

Murphy, JM ;

Hapke, M ;

Ishiyama, T ;

Miyaura, N ;

Hartwig, JF .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (41) :14263-14278

[6] A SIMPLE, GENERAL-SYNTHESIS OF 1-ALKYNYLDIISOPROPOXYBORANES [J].

BROWN, HC ;

BHAT, NG ;

SREBNIK, M .

TETRAHEDRON LETTERS, 1988, 29 (22) :2631-2634

[7] Steric and chelate directing effects in aromatic borylation [J].

Cho, JY ;

Iverson, CN ;

Smith, MR .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (51) :12868-12869

[8] Selective Ir-catalysed borylation of polycyclic aromatic hydrocarbons: structures of naphthalene-2,6-bis(boronate), pyrene-2,7-bis(boronate) and perylene-2,5,8,11-tetra(boronate) esters [J].

Coventry, DN ;

Batsanov, AS ;

Goeta, AE ;

Howard, JAK ;

Marder, TB ;

Perutz, RN .

CHEMICAL COMMUNICATIONS, 2005, (16) :2172-2174

[9] A regioselective cycloaddition route to isoxazoleboronic esters [J].

Davies, MW ;

Wybrow, RAJ ;

Johnson, CN ;

Harrity, JPA .

CHEMICAL COMMUNICATIONS, 2001, (17) :1558-1559

[10] A novel and highly regioselective Cr-mediated route to functionalised quinone boronic ester derivatives [J].

Davies, MW ;

Johnson, CN ;

Harrity, JPA .

CHEMICAL COMMUNICATIONS, 1999, (20) :2107-2108

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