Facile dearomatizing radical arylation of furan and thiophene

被引:19
作者
Crich, D [1 ]
Patel, M [1 ]
机构
[1] Univ Illinois, Dept Chem, Chicago, IL 60607 USA
关键词
D O I
10.1021/ol051027w
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
[GRAPHICS] In the presence of catalytic diphenyl diselenide, reduced in situ to benzeneselenol, tributyltin hydride and V-70 promote the addition of aryl iodides to furan and thiophene. The adduct radicals are trapped by the selenol to give the 2-aryl-2,3-dihydro and 2-aryl-2,5-dihydro heterocyclic products. When the iodide is an o-iodophenol, a cyclization follows the radical addition and provides bridged bicyclic acetals.
引用
收藏
页码:3625 / 3628
页数:4
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共 41 条
[1]   The mechanism of Bu3SnH-mediated homolytic aromatic substitution [J].
Beckwith, ALJ ;
Bowry, VW ;
Bowman, WR ;
Mann, E ;
Parr, J ;
Storey, JMD .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (01) :95-98
[2]   HOMOLYTIC AROMATIC SUBSTITUTION OF HETEROCYCLIC COMPOUNDS .2. PHENYLATION OF FURAN [J].
BENATI, L ;
LABARBA, N ;
TIECCO, M ;
TUNDO, A .
JOURNAL OF THE CHEMICAL SOCIETY B-PHYSICAL ORGANIC, 1969, (09) :1253-&
[3]   HOMOLYTIC AROMATIC SUBSTITUTION OF HETEROCYCLIC COMPOUNDS .I. DECOMPOSITION OF PHENYLAZOTRIPHENYLMETHANE IN THIOPHEN [J].
CAMAGGI, CM ;
LEARDINI, R ;
TIECCO, M ;
TUNDO, A .
JOURNAL OF THE CHEMICAL SOCIETY B-PHYSICAL ORGANIC, 1969, (09) :1251-&
[4]   RATE CONSTANTS AND ARRHENIUS PARAMETERS FOR THE REACTIONS OF PRIMARY, SECONDARY, AND TERTIARY ALKYL RADICALS WITH TRI-NORMAL-BUTYLTIN HYDRIDE [J].
CHATGILIALOGLU, C ;
INGOLD, KU ;
SCAIANO, JC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1981, 103 (26) :7739-7742
[5]   Radical clock reactions under pseudo-first-order conditions using catalytic quantities of diphenyl diselenide. A Se-77- and Sn-119-NMR study of the reaction of tributylstannane diphenyl diselenide [J].
Crich, D ;
Jiao, XY ;
Yao, QW ;
Harwood, JS .
JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (07) :2368-2373
[6]   Direct synthesis of heterobiaryls by radical addition to pyridine: Expeditious synthesis of chelating ligands [J].
Crich, D ;
Patel, M .
HETEROCYCLES, 2004, 64 :499-504
[7]   Synthesis of a 4,6-disubstituted dibenzofuran β-sheet initiator by reductive radical arylation of benzene [J].
Crich, D ;
Grant, D .
JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (06) :2384-2386
[8]   Synthesis of carbazomycin B by radical arylation of benzene [J].
Crich, D ;
Rumthao, S .
TETRAHEDRON, 2004, 60 (07) :1513-1516
[9]   Free-radical chemistry of lactones: Fragmentation of beta-lactones. The beneficial effect of catalytic benzeneselenol on chain propagation [J].
Crich, D ;
Mo, XS .
JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (25) :8624-8625
[10]   Rapid assembly of tetrahydrodibenzofurans and tetrahydrocarbazoles from benzene and o-iodophenols and o-iodoanilines:: reductive radical arylation of benzene in action [J].
Crich, D ;
Sannigrahi, M .
TETRAHEDRON, 2002, 58 (17) :3319-3322