(Diacetoxyiodo)benzene-lithium bromide as a convenient electrophilic Br+ source

被引：85

作者：

Braddock, DC ^{[1
]}

Cansell, G

Hermitage, SA

机构：

[1] Univ London Imperial Coll Sci Technol & Med, Dept Chem, London SW7 2AZ, England

[2] GlaxoSmithKline Ltd, Med Res Ctr, Stevenage SG1 2NY, Herts, England

来源：

SYNLETT | 2004年 / 03期

关键词：

electrophilic aromatic substitution; electrophilic addition; bromine; alkenes; hypervalent iodine;

D O I：

10.1055/s-2004-815410

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A mild and versatile procedure for the bromination of olefins and activated arenes by in situ generation of 'Br+' using (diacetoxyiodo)benzene and lithium bromide is presented. The reactions were carried out in open vessels at room temperature and were typically complete in 30 minutes. The brominated products were isolated by column chromatography, which also allowed for the isolation of the iodobenzene by-product for recycle.

引用

页码：461 / 464

页数：4

共 26 条

[11] GOEHRING RR, 1995, ENCY REAGENTS ORGANI, V1, P679
[12] Hashem MA, 1998, SYNLETT, P195
[13] Application of polymer-supported electrophilic reagents for the 1,2-functionalization of glycals
Kirschning, A
Jesberger, M
Monenschein, H
[J]. TETRAHEDRON LETTERS, 1999, 40 (51) : 8999 - 9002
[14] An efficient and regioselective oxybromination of aromatic compounds using potassium bromide and Oxone®
Narender, N
Srinivasu, P
Prasad, MR
Kulkarni, SJ
Raghavan, KV
[J]. SYNTHETIC COMMUNICATIONS, 2002, 32 (15) : 2313 - 2318
[15] Liquid phase regioselective bromination of aromatic compounds over HZSM-5 catalyst
Narender, N
Srinivasu, P
Kulkarni, SJ
Raghavan, KV
[J]. SYNTHETIC COMMUNICATIONS, 2000, 30 (20) : 3669 - 3675
[16] Olah G.A., 1998, Onium Ions
[17] Synthesis of 3-bromo derivatives of flavones
Rho, HS
Ko, BS
Kim, HK
Ju, YS
[J]. SYNTHETIC COMMUNICATIONS, 2002, 32 (09) : 1303 - 1310
[18] A facile preparation of 3-haloflavones using hypervalent iodine chemistry
Rho, HS
Ko, BS
Ju, YS
[J]. SYNTHETIC COMMUNICATIONS, 2001, 31 (14) : 2101 - 2106
[19] Mild and regioselective oxidative bromination of anilines using potassium bromide and sodium perborate
Roche, D
Prasad, K
Repic, O
Blacklock, TJ
[J]. TETRAHEDRON LETTERS, 2000, 41 (13) : 2083 - 2085
[20] An efficient chemo and regioselective oxidative nuclear bromination of activated aromatic compounds using lithium bromide and ceric ammonium nitrate
Roy, SC
Guin, C
Rana, KK
Maiti, G
[J]. TETRAHEDRON LETTERS, 2001, 42 (39) : 6941 - 6942

← 1 2 3 →