A Pd(II)-Catalyzed Ring-Expansion Reaction of Cyclic 2-Azidoalcohol Derivatives: Synthesis of Azaheterocycles

被引：112

作者：

Chiba, Shunsuke ^{[1
]}

Xu, Yan-Jun ^{[1
]}

Wang, Yi-Feng ^{[1
]}

机构：

[1] Nanyang Technol Univ, Div Chem & Biol Chem, Sch Phys & Math Sci, Singapore 637371, Singapore

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2009年 / 131卷 / 36期

关键词：

PALLADIUM-CATALYZED ARYLATION; CARBON-CARBON BOND; C-H BOND; TERT-CYCLOBUTANOLS; CLEAVAGE; NITRILES; AZIDES; CYCLIZATION; AMINATION; CHEMISTRY;

D O I：

10.1021/ja9049564

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A Pd(II)-catalyzed ring expansion-reaction of cyclic 2-azidoalcohol derivatives was found to proceed via an unprecedented C-C bond cleavage-C-N bond formation sequence, providing substituted azaheterocycles.

引用

页码：12886 / +

页数：3

共 31 条

[1]

Barz M, 1998, ANGEW CHEM INT EDIT, V37, P2262, DOI 10.1002/(SICI)1521-3773(19980904)37:16<2262::AID-ANIE2262>3.0.CO

[2]

2-X

[3] Coordination chemistry of organic azides and amination reactions catalyzed by transition metal complexes [J].

Cenini, Sergio ;

Gallo, Emma ;

Caselli, Alessandro ;

Ragaini, Fabio ;

Fantauzzi, Simone ;

Piangiolino, Cristiana .

COORDINATION CHEMISTRY REVIEWS, 2006, 250 (11-12) :1234-1253

[4] Synthesis of 1-azaazulenes from cycloheptatrienylmethyl ketone O-pentafluorobenzoyloximes by palladium-catalyzed cyclization and oxidation [J].

Chiba, S ;

Kitamura, M ;

Saku, O ;

Narasaka, K .

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 2004, 77 (04) :785-796

[5] SOME REACTIONS OF ALICYCLIC ALPHA-AZIDOKETONES [J].

EDWARDS, OE ;

PURUSHOTHAMAN, KK .

CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1964, 42 (03) :712-&

[6] Palladium-Catalyzed Annulation of Acyloximes with Arynes (or Alkynes) Synthesis of Phenanthridines and Isoquinolines [J].

Gerfaud, Thibaud ;

Neuville, Luc ;

Zhu, Jieping .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (03) :572-577

[7] Synthesis of doubly unsaturated aldehydes and ketones by a novel beta-decarbopalladation [J].

Harayama, H ;

Kuroki, T ;

Kimura, M ;

Tanaka, S ;

Tamaru, Y .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1997, 36 (21) :2352-2354

[8] Palladium-catalyzed stereo- and regiospecific allylation of aryl halides with homoallyl alcohols via retro-allylation:: Selective generation and use of σ-allylpalladium [J].

Hayashi, S ;

Hirano, K ;

Yorimitsu, H ;

Oshima, K .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (07) :2210-2211

[9] Radical fragmentation of β-hydroxy azides.: Synthesis of chiral nitriles [J].

Hernández, R ;

León, EI ;

Moreno, P ;

Suárez, E .

JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (26) :8974-8975

[10] Transition metal-catalyzed carbon-carbon bond activation [J].

Jun, CH .

CHEMICAL SOCIETY REVIEWS, 2004, 33 (09) :610-618

← 1 2 3 4 →