Gold(I)-catalyzed intramolecular hydroamination of alkyne with trichloroacetimidates

被引:129
作者
Kang, Ji-Eun [1 ]
Kim, Hak-Beom [1 ]
Lee, Jin-Woo [1 ]
Shin, Seunghoon [1 ]
机构
[1] Hanyang Univ, Dept Chem, Seoul 133791, South Korea
关键词
D O I
10.1021/ol061307r
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A study on the gold (I)-catalyzed intramolecular hydroamination of trichloroacetimidates derived from propargyl and homopropargyl alcohols is described. In the presence of 2 - 5 mol % of cationic Au(I) complex, a variety of trichloroacetimidates undergo efficient hydroamination under an exceptionally mild condition. An orthogonality of the current catalytic protocol with those using a stoichiometric electrophile as well as a preliminary synthetic application as a stable precursor of 2-acylamino-1,3-diene has been demonstrated.
引用
收藏
页码:3537 / 3540
页数:4
相关论文
共 32 条
[1]   Use of group 4 bis(sulfonamido) complexes in the intramolecular hydroamination of alkynes and allenes [J].
Ackermann, L ;
Bergman, RG ;
Loy, RN .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (39) :11956-11963
[2]   Amines made easily: A highly selective hydroaminomethylation of olefins [J].
Ahmed, M ;
Seayad, AM ;
Jackstell, R ;
Beller, M .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (34) :10311-10318
[3]   Chiral lanthanide complexes: Coordination chemistry and applications [J].
Aspinall, HC .
CHEMICAL REVIEWS, 2002, 102 (06) :1807-1850
[4]   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
[5]   Gold(I)-catalyzed formation of 4-alkylidene-1,3-dioxolan-2-ones from propargylic tert-butyl carbonates [J].
Buzas, A ;
Gagosz, F .
ORGANIC LETTERS, 2006, 8 (03) :515-518
[6]   STEREOCONTROLLED CYCLOFUNCTIONALIZATIONS OF DOUBLE-BONDS THROUGH HETEROCYCLIC INTERMEDIATES [J].
CARDILLO, G ;
ORENA, M .
TETRAHEDRON, 1990, 46 (10) :3321-3408
[7]   Synthesis and Diels-Alder reactions of 2-acetamido-3-phenylthio-buta-1,3-diene and its derivatives [J].
Chou, SSP ;
Chow, TJ ;
Hsu, CH ;
Yang, CD ;
Long, SH ;
Lin, CD .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1997, (11) :1691-1697
[8]   Gold(I)-catalyzed intramolecular hydroamination of alkenyl carbamates [J].
Han, XQ ;
Widenhoefer, RA .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (11) :1747-1749
[9]   Gold catalysis:: Mild conditions for the synthesis of oxazoles from N-propargylcarboxamides and mechanistic aspects [J].
Hashmi, ASK ;
Weyrauch, JP ;
Frey, W ;
Bats, JW .
ORGANIC LETTERS, 2004, 6 (23) :4391-4394
[10]  
Hashmi ASK, 2004, GOLD BULL, V37, P51