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Literature DB >> 19046068

A novel synthetic route to 3-sulfenyl- and 3-selenylindoles by n-Bu4NI-induced electrophilic cyclization.

Yu Chen¹, Chul-Hee Cho, Richard C Larock.

Abstract

3-Sulfenyl- and 3-selenylindoles are prepared in excellent yields by the palladium/copper-catalyzed crossing coupling of N,N-dialkyl-o-iodoanilines and terminal alkynes, followed by electrophilic cyclization with arylsulfenyl chlorides and arylselenyl chlorides in the presence of a stoichiometric amount of n-Bu(4)NI.

Entities: Chemical Disease

Mesh：

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Year: 2009 PMID： 19046068 PMCID： PMC2631273 DOI： 10.1021/ol8021287

Source DB: PubMed Journal: Org Lett ISSN： 1523-7052 Impact factor: 6.005

22 in total

1. Synthesis of 2,3-disubstituted benzo[b]furans by the palladium-catalyzed coupling of o-iodoanisoles and terminal alkynes, followed by electrophilic cyclization.

Authors: Dawei Yue; Tuanli Yao; Richard C Larock
Journal: J Org Chem Date: 2005-12-09 Impact factor: 4.354

2. An efficient synthesis of coumestrol and coumestans by iodocyclization and Pd-catalyzed intramolecular lactonization.

Authors: Tuanli Yao; Dawei Yue; Richard C Larock
Journal: J Org Chem Date: 2005-11-25 Impact factor: 4.354

3. Synthesis of substituted isoquinolines by electrophilic cyclization of iminoalkynes.

Authors: Qinhua Huang; Jack A Hunter; Richard C Larock
Journal: J Org Chem Date: 2002-05-17 Impact factor: 4.354

4. Synthesis of 3-iodoindoles by the Pd/Cu-catalyzed coupling of N,N-dialkyl-2-iodoanilines and terminal acetylenes, followed by electrophilic cyclization.

Authors: Dawei Yue; Tuanli Yao; Richard C Larock
Journal: J Org Chem Date: 2006-01-06 Impact factor: 4.354

5. Synthesis of 2,3-disubstituted benzo[b]thiophenes via palladium-catalyzed coupling and electrophilic cyclization of terminal acetylenes.

Authors: Dawei Yue; Richard C Larock
Journal: J Org Chem Date: 2002-03-22 Impact factor: 4.354

6. Synthesis of isocoumarins and alpha-pyrones via electrophilic cyclization.

Authors: Tuanli Yao; Richard C Larock
Journal: J Org Chem Date: 2003-07-25 Impact factor: 4.354

7. Synthesis of 3-iodoindoles by electrophilic cyclization of N,N-dialkyl-2-(1-alkynyl)anilines.

Authors: Dawei Yue; Richard C Larock
Journal: Org Lett Date: 2004-03-18 Impact factor: 6.005

8. The synthesis of highly substituted isoxazoles by electrophilic cyclization: an efficient synthesis of valdecoxib.

Authors: Jesse P Waldo; Richard C Larock
Journal: J Org Chem Date: 2007-11-03 Impact factor: 4.354

Review 9. Indole-3-carbinol as a chemopreventive and anti-cancer agent.

Authors: Jing-Ru Weng; Chen-Hsun Tsai; Samuel K Kulp; Ching-Shih Chen
Journal: Cancer Lett Date: 2008-03-07 Impact factor: 8.679

Review 10. Human papillomavirus, cervical carcinogenesis and chemoprevention with Indole derivates - a review of pathomechanisms.

Authors: Gudrun C Rieck; Alison N Fiander
Journal: Mol Nutr Food Res Date: 2008-01 Impact factor: 5.914

6 in total

1. An oxidation of benzyl methyl ethers with nbs that selectively affords either aromatic aldehydes or aromatic methyl esters.

Authors: Abdelrahman S Mayhoub; Arindam Talukdar; Mark Cushman
Journal: J Org Chem Date: 2010-05-21 Impact factor: 4.354

2. Synthesis of 3-sulfenyl- and 3-selenylindoles by the Pd/Cu-catalyzed coupling of N,N-dialkyl-2-iodoanilines and terminal alkynes, followed by n-Bu(4)NI-induced electrophilic cyclization.

Authors: Yu Chen; Chul-Hee Cho; Feng Shi; Richard C Larock
Journal: J Org Chem Date: 2009-09-04 Impact factor: 4.354