Biaryl synthesis via palladium-catalyzed aryne multicomponent coupling

被引:56
作者
Henderson, Jaclyn L. [1 ]
Edwards, Andrew S. [2 ]
Greaney, Michael F. [1 ]
机构
[1] Univ Edinburgh, Sch Chem, Edinburgh EH9 3JJ, Midlothian, Scotland
[2] Organon Res Labs Ltd, Newhouse ML1 5SH, Lanark, Scotland
关键词
D O I
10.1021/ol702584t
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Aryl iodides have been introduced as electrophiles in the three-component Heck coupling of arynes. Following optimization studies to favor three- versus two-component coupling, the reaction proceeds in good yield to afford a variety of functionalized biaryls.
引用
收藏
页码:5589 / 5592
页数:4
相关论文
共 37 条
[1]   Carbocyclization of aromatic iodides, bicyclic alkenes, and benzynes involving a palladium-catalyzed C-H bond activation as a key step [J].
Bhuvaneswari, Sivakolundu ;
Jeganmohan, Masilamani ;
Cheng, Chien-Hong .
ORGANIC LETTERS, 2006, 8 (24) :5581-5584
[2]   Aryl to aryl palladium migration in the Heck and Suzuki coupling of o-halobiaryls [J].
Campo, Marino A. ;
Zhang, Haiming ;
Yao, Tuanli ;
Ibdah, Abdellatif ;
McCulla, Ryan D. ;
Huang, Qinhua ;
Zhao, Jian ;
Jenks, William S. ;
Larock, Richard C. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (19) :6298-6307
[3]   Catalytic carbonylation reactions of benzyne derivatives [J].
Chatani, N ;
Kamitani, A ;
Oshita, M ;
Fukumoto, Y ;
Murai, S .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (50) :12686-12687
[4]   Palladium in action:: domino coupling and allylic substitution reactions for the efficient construction of complex organic molecules [J].
de Meijere, A ;
Bräse, S .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1999, 576 (1-2) :88-110
[5]   Organometallic generation and capture of ortho-arynes [J].
Dyke, Alan M. ;
Hester, Alison J. ;
Lloyd-Jones, Guy C. .
SYNTHESIS-STUTTGART, 2006, (24) :4093-4112
[6]   Structure-activity relationship of triaryl propionic acid analogues on the human EP3 prostanoid receptor [J].
Gallant, M ;
Belley, M ;
Carrière, MC ;
Chateauneuf, A ;
Denis, D ;
Lachance, N ;
Lamontagne, S ;
Metters, KM ;
Sawyer, N ;
Slipetz, D ;
Truchon, JF ;
Labelle, M .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2003, 13 (21) :3813-3816
[7]  
Guitián E, 2005, TOP ORGANOMETAL CHEM, V14, P109
[8]   Three-component coupling of benzyne: Domino intermolecular carbopalladation [J].
Henderson, Jaclyn L. ;
Edwards, Andrew S. ;
Greaney, Michael F. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (23) :7426-7427
[9]   The stereochemistry of palladium catalysed cyclisation reactions .C. Cascade reactions [J].
Heumann, A ;
Reglier, M .
TETRAHEDRON, 1996, 52 (28) :9289-9346
[10]   Nickel-catalyzed highly chemoselective cocyclotrimerization of arynes with allenes: a novel method for 10-methylene-9,10-dihydrophenanthrenes [J].
Hsieh, JC ;
Rayabarapu, DK ;
Cheng, CH .
CHEMICAL COMMUNICATIONS, 2004, (05) :532-533