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

被引：169

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
Ackermann, L
Althammer, A
Born, R
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (16) : 2619 - 2622
[2] Aryl-aryl bond formation by transition-metal-catalyzed direct arylation
Alberico, Dino
Scott, Mark E.
Lautens, Mark
[J]. 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
ALBRECHT, K
REISER, O
WEBER, M
KNIERIEM, B
DEMEIJERE, A
[J]. TETRAHEDRON, 1994, 50 (02) : 383 - 401
[4] Enantioselective synthesis of 2-arylpiperidines from chiral lactams.: A concise synthesis of (-)-anabasine
Amat, M
Cantó, M
Llor, N
Bosch, J
[J]. CHEMICAL COMMUNICATIONS, 2002, (05) : 526 - 527
[5] PALLADIUM-CATALYZED CYCLIZATION OF 2-SUBSTITUTED HALOGENOARENES BY DEHYDROHALOGENATION
AMES, DE
OPALKO, A
[J]. TETRAHEDRON, 1984, 40 (10) : 1919 - 1925
[6] Synthesis of 2-substituted pyridines via a regiospecific alkylation, alkynylation, and arylation of pyridine N-oxides
Andersson, Hans
Almqvist, Fredrik
Olsson, Roger
[J]. 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
Buffat, MGP
[J]. 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
Campeau, LC
Rousseaux, S
Fagnou, K
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (51) : 18020 - 18021

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