Two palladium-catalyzed domino reactions from one set of substrates/reagents:: Efficient synthesis of substituted indenes and cis-stilbenoid hydrocarbons from the same internal alkynes and hindered grignard reagents

被引：30

作者：

Dong, Cheng-Guo ^{[1
]}

Yeung, Pik

Hu, Qiao-Sheng

机构：

[1] CUNY Coll Staten Isl, Dept Chem, Staten Isl, NY 10314 USA

[2] CUNY, Grad Ctr, Staten Isl, NY 10314 USA

来源：

ORGANIC LETTERS | 2007年 / 9卷 / 02期

关键词：

D O I：

10.1021/ol062885a

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Two types of domino reactions from the same internal alkynes and hindered Grignard reagents based on carbopalladation, Pd-catalyzed cross-coupling reaction, and a C-H activation strategy are described. The realization of these domino reactions relied on the control of the use of the ligand and the reaction temperature. Our study provides efficient access to useful polysubstituted indenes and cis-substituted stilbenes and may offer a new means of development of tandem/domino reactions in a more efficient way.

引用

页码：363 / 366

页数：4

共 58 条

[11] Annulative tandem reactions based on Pd0/tBu3P-catalyzed cross-coupling and C(sp3)-H bond activation
Dong, CG
Hu, QS
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (14) : 2289 - 2292
[12] Pd(OAc)2-catalyzed Domino reactions of 1-chloro-2-haloarenes and 2-haloaryl tosylates with hindered Grignard reagents via palladium-associated arynes
Dong, Cheng-Guo
Hu, Qiao-Sheng
[J]. ORGANIC LETTERS, 2006, 8 (22) : 5057 - 5060
[13] TRANSITION-METAL-CATALYZED ANNELATION REACTIONS .5. PALLADIUM-CATALYZED C-H ACTIVATION OF TERT-BUTYL GROUPS - A SIMPLE SYNTHESIS OF 1,2-DIHYDROCYCLOBUTABENZENE DERIVATIVES
DYKER, G
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1994, 33 (01): : 103 - 105
[14] PALLADIUM-CATALYZED C-H ACTIVATION OF METHOXY GROUPS - A FACILE SYNTHESIS OF SUBSTITUTED 6H-DIBENZO[B,D]PYRANS
DYKER, G
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1992, 31 (08): : 1023 - 1025
[15] PALLADIUM-CATALYZED C-H ACTIVATION AT METHOXY GROUPS FOR CROSS-COUPLING REACTIONS - A NEW APPROACH TO SUBSTITUTED BENZO[B]FURANS
DYKER, G
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (23) : 6426 - 6428
[16] Dyker G., 2005, Handbook of C-H Transformations, V2
[17] A domino amidation route to indolines and indoles: Rapid syntheses of anhydrolycorinone, hippadine, oxoassoanine, and pratosine
Ganton, MD
Kerr, MA
[J]. ORGANIC LETTERS, 2005, 7 (21) : 4777 - 4779
[18] Synthesis of indenes via palladium-catalyzed carboannulation of diethyl 2-(2-(1-alkynyl)phenyl)malonate and organic halides
Guo, LN
Duan, XH
Bi, HP
Liu, XY
Liang, YM
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (08) : 3325 - 3327
[19] Palladium-catalyzed synthesis of 2,1′-disubstituted tetrahydrofurans from γ-hydroxy internal alkenes.: Evidence for alkene insertion into a Pd-O bond and stereochemical scrambling via β-hydride elimination
Hay, MB
Wolfe, JP
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (47) : 16468 - 16476
[20] Three-component coupling of benzyne: Domino intermolecular carbopalladation
Henderson, Jaclyn L.
Edwards, Andrew S.
Greaney, Michael F.
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (23) : 7426 - 7427

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