One-pot four-component reaction:: Aqueous TiCl3/PhN2+-mediated alkyl radical addition to imines generated in situ

被引:37
作者
Cannella, R [1 ]
Clerici, A [1 ]
Pastori, N [1 ]
Regolini, E [1 ]
Porta, O [1 ]
机构
[1] Politecn Milan, Sez Chim, Dipartimento Chim Mat & Ingn Chim Giulio Natta, I-20131 Milan, Italy
关键词
D O I
10.1021/ol047595d
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Ti(III)-induced free-radical decomposition of a phenyldiazonium salt, followed by phenyl radical iodine-atom abstraction from alkyl iodides, leads to a one-pot selective alkyl radical addition to the C-atom of imines generated in situ under aqueous acidic conditions.
引用
收藏
页码:645 / 648
页数:4
相关论文
共 32 条
[1]   ELECTRON SPIN RESONANCE STUDIES .21. REACTIONS OF PHENYL AND SUBSTITUTED PHENYL RADICALS IN AQUEOUS SOLUTION [J].
BECKWITH, AL ;
NORMAN, ROC .
JOURNAL OF THE CHEMICAL SOCIETY B-PHYSICAL ORGANIC, 1969, (04) :403-&
[2]   Et3B- and Et2Zn-mediated radical additions to glyoxylate imines, compared stereoinductions [J].
Bertrand, MP ;
Coantic, S ;
Feray, L ;
Nouguier, R ;
Perfetti, P .
TETRAHEDRON, 2000, 56 (24) :3951-3961
[3]   Additions of organometallic reagents to C=N bonds: Reactivity and selectivity [J].
Bloch, R .
CHEMICAL REVIEWS, 1998, 98 (04) :1407-1438
[4]  
Boulton aj, 1974, ADV HETEROCYCLIC CHE, V16, P123
[5]   GENERATION OF AMINYL RADICALS USING SULFENAMIDES AS SYNTHETIC PRECURSORS [J].
BOWMAN, WR ;
CLARK, DN ;
MARMON, RJ .
TETRAHEDRON, 1994, 50 (04) :1275-1294
[6]   ARYLATIVE AMINATION OF ALDEHYDES PROMOTED BY AQUEOUS TITANIUM TRICHLORIDE [J].
CLERICI, A ;
PORTA, O .
TETRAHEDRON LETTERS, 1990, 31 (14) :2069-2072
[7]  
CLERICI A, 1973, CHIM ITAL, V103, P171
[8]   TITANIUM(IV) CHLORIDE PROMOTED CONDENSATION OF ORTHO-AMINONITRILES WITH DELTA-VALEROLACTONE [J].
DESAI, MC ;
THADEIO, PF .
TETRAHEDRON LETTERS, 1989, 30 (39) :5223-5226
[9]   Addition of carbon-centered radicals to imines and related compounds [J].
Friestad, GK .
TETRAHEDRON, 2001, 57 (26) :5461-5496
[10]   Intermolecular addition of alkyl radicals to imines in the absence and in the presence of a Lewis acid [J].
Halland, N ;
Jorgensen, KA .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2001, (11) :1290-1295