Palladium-catalyzed direct C-H arylation of N-iminopyridinium ylides:: Application to the synthesis of (±)-anabasine

被引：171

作者：

Larivee, Alexandre ^{[1
]}

Mousseau, James J. ^{[1
]}

Charette, Andre B. ^{[1
]}

机构：

[1] Univ Montreal, Dept Chem, Montreal, PQ H3C 3J7, Canada

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2008年 / 130卷 / 01期

关键词：

D O I：

10.1021/ja710073n

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Palladium-catalyzed direct C-H arylation of N-iminopyridinium ylides provides a powerful and versatile method for the synthesis of functionalized piperidines in good yields. Chemoselective functionalization of the pyridinium ring in the presence of a pyridine substituent is possible as exemplified by the expedient synthesis of anabasine in 61% overall yield over three steps.

引用

页码：52 / +

页数：4

共 43 条

[1] Catalytic arylation reactions by C-H bond activation with aryl tosylates [J].

Ackermann, L ;

Althammer, A ;

Born, R .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (16) :2619-2622

[2] Aryl-aryl bond formation by transition-metal-catalyzed direct arylation [J].

Alberico, Dino ;

Scott, Mark E. ;

Lautens, Mark .

CHEMICAL REVIEWS, 2007, 107 (01) :174-238

[3] PALLADIUM-CATALYZED DOMINO COUPLING REACTIONS OF ARYL HALIDES WITH NORBORNENE AND NORBORNENE DERIVATIVES - A SIMPLE ROUTE TO POLYCYCLIC AROMATIC-COMPOUNDS [J].

ALBRECHT, K ;

REISER, O ;

WEBER, M ;

KNIERIEM, B ;

DEMEIJERE, A .

TETRAHEDRON, 1994, 50 (02) :383-401

[4] Enantioselective synthesis of 2-arylpiperidines from chiral lactams.: A concise synthesis of (-)-anabasine [J].

Amat, M ;

Cantó, M ;

Llor, N ;

Bosch, J .

CHEMICAL COMMUNICATIONS, 2002, (05) :526-527

[5] PALLADIUM-CATALYZED CYCLIZATION OF 2-SUBSTITUTED HALOGENOARENES BY DEHYDROHALOGENATION [J].

AMES, DE ;

OPALKO, A .

TETRAHEDRON, 1984, 40 (10) :1919-1925

[6] Synthesis of 2-substituted pyridines via a regiospecific alkylation, alkynylation, and arylation of pyridine N-oxides [J].

Andersson, Hans ;

Almqvist, Fredrik ;

Olsson, Roger .

ORGANIC LETTERS, 2007, 9 (07) :1335-1337

[7]

Andrés JM, 2000, EUR J ORG CHEM, V2000, P1719

[8]

Barco A, 2001, EUR J ORG CHEM, V2001, P975

[9] Synthesis of piperidines [J].

Buffat, MGP .

TETRAHEDRON, 2004, 60 (08) :1701-1729

[10] A solution to the 2-pyridyl organometallic cross-coupling problem:: Regioselective catalytic direct arylation of pyridine N-oxides [J].

Campeau, LC ;

Rousseaux, S ;

Fagnou, K .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (51) :18020-18021

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