Regioselective dicouplings: Application to differentially substituted pyrroles

被引：65

作者：

Handy, ST ^{[1
]}

Sabatini, JJ ^{[1
]}

机构：

[1] SUNY Binghamton, Dept Chem, Binghamton, NY 13902 USA

来源：

ORGANIC LETTERS | 2006年 / 8卷 / 08期

关键词：

D O I：

10.1021/ol0530981

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

In an effort to develop a more concise route to differentially substituted pyrroles (such as that found in the lamellarins), a completely regioselective one-pot double Suzuki coupling has been discovered. The key feature is the use of a ligand-free palladium catalyst under optimized conditions, which results only in coupling of the C5 bromide. At this point, addition of a second boronic acid and a phosphine ligand enables coupling at the remaining C4 bromide.

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页码：1537 / 1539

页数：3

相关论文

共 11 条

[1] PYRROLE CHEMISTRY .4. PREPARATION AND SOME REACTIONS OF BROMINATED PYRROLE DERIVATIVES [J].

ANDERSON, HJ ;

LEE, SF .

CANADIAN JOURNAL OF CHEMISTRY, 1965, 43 (02) :409-&

[2] A concise synthesis of 2,4-disubstituted pyridines: A convenient synthesis of 2-bromo-4-iodopyridine via halogen dance and its successive one-pot disubstitutions [J].

Duan, XF ;

Li, XH ;

Li, FY ;

Huang, CH .

SYNTHESIS-STUTTGART, 2004, (16) :2614-2616

[3] KINETICS OF OXIDATIVE ADDITION OF ZEROVALENT PALLADIUM TO AROMATIC IODIDES [J].

FAUVARQUE, JF ;

PFLUGER, F ;

TROUPEL, M .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1981, 208 (03) :419-427

[4] Chemistry and biology of roseophilin and the prodigiosin alkaloids:: A survey of the last 2500 years [J].

Fürstner, A .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (31) :3582-3603

[5] Approaches to the synthesis of the lamellarins and related natural products. A review [J].

Handy, ST ;

Zhang, YN .

ORGANIC PREPARATIONS AND PROCEDURES INTERNATIONAL, 2005, 37 (05) :411-+

[6] A modular synthesis of the lamellarins: Total synthesis of lamellarin G trimethyl ether [J].

Handy, ST ;

Zhang, YN ;

Bregman, H .

JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (07) :2362-2366

[7] An unusual dehalogenation in the Suzuki coupling of 4-bromopyrrole-2-carboxylates [J].

Handy, ST ;

Bregman, H ;

Lewis, J ;

Zhang, XL ;

Zhang, YN .

TETRAHEDRON LETTERS, 2003, 44 (03) :427-430

[8] SUCCESSIVE DIARYLATION AT THE CARBON POSITIONS (2/4 AND 2/5) OF 1H-IMIDAZOLE AND ITS APPLICATION TO THE TOTAL SYNTHESIS OF NORTOPSENTIN-D [J].

KASWASAKI, I ;

YAMASHITA, M ;

OHTA, S .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1994, (18) :2085-2086

[9]

Li J.-J., 2004, CONT DRUG SYNTHESIS, P113

[10] Air-stable trialkylphosphonium salts: Simple, practical, and versatile replacements for air-sensitive trialkylphosphines. Applications in stoichiometric and catalytic processes [J].

Netherton, MR ;

Fu, GC .

ORGANIC LETTERS, 2001, 3 (26) :4295-4298