A new cascade radical reaction for the synthesis of biaryls and triaryls from benzyl iodoaryl ethers

被引：55

作者：

Harrowven, DC ^{[1
]}

Nunn, MIT

Newman, NA

Fenwick, DR

机构：

[1] Univ Southampton, Dept Chem, Southampton S017 1BJ, Hants, England

[2] Pfizer Global Res & Dev, Discovery Chem, Sandwich CT13 9NJ, Kent, England

来源：

TETRAHEDRON LETTERS | 2001年 / 42卷 / 05期

基金：

英国工程与自然科学研究理事会;

关键词：

radicals and radical reactions; natural products; aromatic chemistry; cascade reactions;

D O I：

10.1016/S0040-4039(00)02111-0

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The paper describes a new method of synthesizing biaryls and triaryls through an intramolecular ipso-substitution reaction initiated by the addition of an aryl radical to a benzyl ether. A tandem variant of the reaction has also been demonstrated. A short synthesis of isoaucuparin 27, a natural product found in the sapwood tissue of Sorbus aucuparia, is also described. (C) 2001 Elsevier Science Ltd. All rights reserved.

引用

页码：961 / 964

页数：4

共 20 条

[1] Novel intramolecular rearrangement of 3-bromo-3,3-difluoroalanine Schiff bases via radical ipso-substitution at the aromatic ring
Amii, H
Kondo, S
Uneyama, K
[J]. CHEMICAL COMMUNICATIONS, 1998, (17) : 1845 - 1846
[2] Stereoselective radical aryl migration from silicon to carbon
Amrein, S
Bossart, M
Vasella, T
Studer, A
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (14) : 4281 - 4288
[3] AROMATIC OXIDATION BY ELECTRON TRANSFER .I. OXIDATIONS OF P-METHOXYTOLUENE
ANDRULIS, PJ
DEWAR, MJS
DIETZ, R
HUNT, RL
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1966, 88 (23) : 5473 - &
[4] [Anonymous], TETRAHEDRON LETT
[5] [Anonymous], TETRAHEDRON LETT
[6] Bonfand E, 2000, SYNLETT, P475
[7] Bu3SnH mediated oxidative radical cyclisations:: synthesis of 6H-benzo[c]chromen-6-ones
Bowman, WR
Mann, E
Parr, J
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2000, (17): : 2991 - 2999
[8] Atom transfer radical cyclisations of activated and unactivated N-allylhaloacetamides and N-homoallylhaloacetamides using chiral and non-chiral copper complexes
Clark, AJ
De Campo, F
Deeth, RJ
Filik, RP
Gatard, S
Hunt, NA
Lastécouères, D
Thomas, GH
Verlhac, JB
Wongtap, H
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2000, (05): : 671 - 680
[9] Synthesis of biaryls by intramolecular radical transfer: use of phosphinates
Clive, DLJ
Kang, SZ
[J]. TETRAHEDRON LETTERS, 2000, 41 (09) : 1315 - 1319
[10] Stannane-mediated radical addition to arenes. Generation of cyclohexadienyl radicals and increased propagation efficiency in the presence of catalytic benzeneselenol
Crich, D
Hwang, JT
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (08) : 2765 - 2770

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