First hypervalent iodine(III)-catalyzed C-N bond forming reaction:: catalytic spirocyclization of amides to N-fused spirolactams

被引：193

作者：

Dohi, Toshifumi ^{[1
]}

Maruyama, Akinobu ^{[1
]}

Minamitsuji, Yutaka ^{[1
]}

Takenaga, Naoko ^{[1
]}

Kita, Yasuyuki ^{[1
]}

机构：

[1] Osaka Univ, Grad Sch Pharmaceut Sci, Suita, Osaka 5650871, Japan

来源：

CHEMICAL COMMUNICATIONS | 2007年 / 12期

关键词：

D O I：

10.1039/b616510a

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A protic solvent, 2,2,2-trifluoroethanol (CF3CH2OH), was successfully introduced into hypervalent iodine(III)-involved catalytic cycles as an effective solvent, and the first iodoarene-catalyzed intramolecular carbon-nitrogen bond forming reaction was achieved under strong acid-free and mild conditions.

引用

页码：1224 / 1226

页数：3

共 35 条

[1] Oxidative synthesis of azacyclic derivatives through the nitrenium ion: application of a hypervalent iodine species electrochemically generated from iodobenzene
Amano, Yoshiharu
Nishiyama, Shigeru
[J]. TETRAHEDRON LETTERS, 2006, 47 (37) : 6505 - 6507
[2] [Anonymous], CHEM HYPERVALENT COM
[3] Fluorinated alcohols:: A new medium for selective and clean reaction
Bégué, JP
Bonnet-Delpon, D
Crousse, B
[J]. SYNLETT, 2004, (01) : 18 - 29
[4] Ortho-substituted iodobenzenes as novel organocatalysts for bromination of alkenes
Braddock, D. Christopher
Cansell, Gemma
Hermitage, Stephen A.
[J]. CHEMICAL COMMUNICATIONS, 2006, (23) : 2483 - 2485
[5] New oxidative transformations of phenolic and indolic oxazolines: An avenue to useful azaspirocyclic building blocks
Braun, NA
Ousmer, M
Bray, JD
Bouchu, D
Peters, K
Peters, EM
Ciufolini, MA
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (14) : 4397 - 4408
[6] OXIDATIVELY ASSISTED NUCLEOPHILIC-SUBSTITUTION ELIMINATION OF ALKYL IODIDES IN ALCOHOLIC MEDIA - A FURTHER STUDY
DAVIDSON, RI
KROPP, PJ
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1982, 47 (10) : 1904 - 1909
[7] Versatile hypervalent-iodine(III)-catalyzed oxidations with m-chloroperbenzoic acid as a cooxidant
Dohi, T
Maruyama, A
Yoshimura, M
Morimoto, K
Tohma, H
Kita, Y
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (38) : 6193 - 6196
[8] A unique site-selective reaction of ketones with new recyclable hypervalent iodine(III) reagents based on a tetraphenylmethane structure
Dohi, T
Maruyama, A
Yoshimura, M
Morimoto, K
Tohma, H
Shiro, M
Kita, Y
[J]. CHEMICAL COMMUNICATIONS, 2005, (17) : 2205 - 2207
[9] Dohi T., 2006, KAGAKU, V61, P68
[10] ELECTROLYTIC PARTIAL FLUORINATION OF ORGANIC-COMPOUNDS .14. ELECTROCHEMISTRY OF HYPERVALENT COMPOUNDS .2. THE FIRST ELECTROSYNTHESIS OF HYPERVALENT IODOBENZENE DIFLUORIDE DERIVATIVES AND ITS APPLICATION TO INDIRECT ANODIC GEM-DIFLUORINATION
FUCHIGAMI, T
FUJITA, T
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (24) : 7190 - 7192

← 1 2 3 4 →