Simple Gold-Catalyzed Synthesis of Benzofulvenesugem-Diaurated Species as "Instant Dual-Activation" Precatalysts

被引:268
作者
Hashmi, A. Stephen K. [1 ]
Braun, Ingo [1 ]
Noesel, Pascal [1 ]
Schaedlich, Johannes [1 ]
Wieteck, Marcel [1 ]
Rudolph, Matthias [1 ]
Rominger, Frank [1 ]
机构
[1] Univ Heidelberg, Inst Organ Chem, D-69120 Heidelberg, Germany
关键词
alkynes; benzofulvenes; gold; homogeneous catalysis; vinylgold intermediates; COMPLEXES; CYCLOISOMERIZATION; CARBENE; BOND; VINYLIDENES; ALLENES; ALKYNES; DIYNES; MODEL;
D O I
10.1002/anie.201109183
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Alkyl-substituted diynes deliver benzofulvenes in a unique gold-catalyzed reaction. The catalytic cycle involves the formation of gold acetylides by alkynyl C-H activation, the formation of vinylidene gold(I) intermediates by dual activation, and alkyl C-H activation by the vinylidene gold(I) species. gem-Diaurated species obtained from the catalysis reactions prove to be highly active catalysts for these conversions. Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
引用
收藏
页码:4456 / 4460
页数:5
相关论文
共 53 条
[1]   Synthesis of a Core Carbon Framework of Cyanosporasides A and B [J].
Aburano, Daislike ;
Inagaki, Fuyuhiko ;
Tomonaga, Shoichirou ;
Mukai, Chisato .
JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (15) :5590-5594
[2]  
Andrianov V. G., 1974, J STRUCT CHEM, V15, P65
[3]  
[Anonymous], 2009, Angew. Chem
[4]   Alternative synthetic methods through new developments in catalysis by gold [J].
Arcadi, Antonio .
CHEMICAL REVIEWS, 2008, 108 (08) :3266-3325
[5]   ATTEMPTS TO PREPARE NEW AROMATIC SYSTEMS .4. CYCLOPENT[A]INDENE [J].
BAKER, W ;
GLOCKLING, F ;
MCOMIE, JFW .
JOURNAL OF THE CHEMICAL SOCIETY, 1951, (DEC) :3357-3361
[6]   New organogold(I) complexes: Synthesis, structure, and dynamic behavior of the polynuclear organogold diphenylmethane and diphenylethane derivatives [J].
Baukova, TV ;
Kuzmina, LG ;
Oleinikova, NA ;
Lemenovskii, DA ;
Blumenfeld, AL .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1997, 530 (1-2) :27-38
[7]  
Benitez D, 2009, NAT CHEM, V1, P482, DOI [10.1038/NCHEM.331, 10.1038/nchem.331]
[8]   Gold-Catalyzed 1,3-Addition of a Sp3-Hybridized C-H Bond to Alkenylcarbenoid Intermediate [J].
Bhunia, Sabyasachi ;
Liu, Rai-Shung .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (49) :16488-+
[9]   Gold-catalyzed cycloisomerization of 1,5-allenynes via dual activation of an ene reaction [J].
Cheong, Paul Ha-Yeon ;
Morganelli, Philip ;
Luzung, Michael R. ;
Houk, K. N. ;
Toste, F. Dean .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (13) :4517-4526
[10]   Gold-Catalyzed Carbon-Heteroatom Bond-Forming Reactions [J].
Corma, A. ;
Leyva-Perez, A. ;
Sabater, Maria J. .
CHEMICAL REVIEWS, 2011, 111 (03) :1657-1712