Intramolecular alkyne hydroalkoxylation and hydroamination catalyzed by iridium hydrides

被引:225
作者
Li, XW [1 ]
Chianese, AR [1 ]
Vogel, T [1 ]
Crabtree, RH [1 ]
机构
[1] Yale Univ, Dept Chem, New Haven, CT 06520 USA
关键词
D O I
10.1021/ol052186i
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Iridium(III) hydrides prove to be air-stable active catalysts for intramolecular hydroalkoxylation and hydroamination of internal alkynes with proximate nucleophiles. The cyclization follows highly selective 6-endo-dig regiochemistry when regioselectivity is an issue.
引用
收藏
页码:5437 / 5440
页数:4
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共 51 条
[1]   Transition-metal-catalyzed addition of heteroatom-hydrogen bonds to alkynes [J].
Alonso, F ;
Beletskaya, IP ;
Yus, M .
CHEMICAL REVIEWS, 2004, 104 (06) :3079-3159
[2]   A new approach to 2,3-disubstituted benzo[b]furans from o-alkynylphenols via 5-endo-dig-iodocyclisation/palladium-catalysed reactions [J].
Arcadi, A ;
Cacchi, S ;
Fabrizi, G ;
Marinelli, F ;
Moro, L .
SYNLETT, 1999, (09) :1432-1434
[3]   AuBr3-catalyzed cyclization of o-(alkynyl)nitrobenzenes.: Efficient synthesis of isatogens and anthranils [J].
Asao, N ;
Sato, K ;
Yamamoto, Y .
TETRAHEDRON LETTERS, 2003, 44 (30) :5675-5677
[4]   AuBr3-catalyzed [4+2] benzannulation between an enynal unit and enol [J].
Asao, N ;
Aikawa, H ;
Yamamoto, Y .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (24) :7458-7459
[5]   Pd(II) acts simultaneously as a Lewis acid and as a transition-metal catalyst: Synthesis of cyclic alkenyl ethers from acetylenic aldehydes [J].
Asao, N ;
Nogami, T ;
Takahashi, K ;
Yamamoto, Y .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (05) :764-765
[6]   AuCl3-catalyzed benzannulation:: Synthesis of naphthyl ketone derivatives from o-alkynylbenzaldehydes with alkynes [J].
Asao, N ;
Takahashi, K ;
Lee, S ;
Kasahara, T ;
Yamamoto, Y .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (43) :12650-12651
[7]   Cyclization of carbonyl groups onto alkynes upon reaction with IPy2BF4 and their trapping with nucleophiles:: A versatile trigger for assembling oxygen heterocycles [J].
Barluenga, J ;
Vázquez-Villa, H ;
Ballesteros, A ;
González, JM .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (30) :9028-9029
[8]   Regioselective synthesis of substituted naphthalenes:: A novel de novo approach based on a metal-free protocol for stepwise cycloaddition of o-alkynylbenzaldehyde derivatives with either alkynes or alkenes [J].
Barluenga, J ;
Váquez-Villa, H ;
Ballesteros, A ;
González, JM .
ORGANIC LETTERS, 2003, 5 (22) :4121-4123
[9]   Catalytic Markovnikov and anti-Markovnikov functionalization of alkenes and alkynes: Recent developments and trends [J].
Beller, M ;
Seayad, J ;
Tillack, A ;
Jiao, H .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (26) :3368-3398
[10]   Regioselective synthesis of natural and unnatural (Z)-3-(1-alkylidene)phthalides and 3-substituted isocoumarins starting from methyl 2-hydroxybenzoates [J].
Bellina, F ;
Ciucci, D ;
Vergamini, P ;
Rossi, R .
TETRAHEDRON, 2000, 56 (16) :2533-2545