Organic letters

Transition-Metal-Free Alkynylation of Aryl Chlorides

T Truong, O Daugulis

Index: Truong, Thanh; Daugulis, Olafs Organic Letters, 2011 , vol. 13, # 16 p. 4172 - 4175

Full Text: HTML

Citation Number: 21

Abstract

Two sets of conditions have been developed for a base-mediated, transition-metal-free alkynylation of aryl chlorides that proceeds via benzyne intermediates. The first set of conditions involves the use of TMPLi base in a pentane/THF mixture at 25° C. The second set involves use of a metal alkoxide base in dioxane at elevated temperature. Reasonable functional group tolerance has been observed. Fluoro, trifluoromethyl, silyl, cyano, and ...

Related Articles:

Monodispersed and Stable Nano Copper (0) from Copper??Aluminium Hydrotalcite: Importance in C C Couplings of Deactivated Aryl Chlorides

[Arundhathi, Racha; Damodara, Dandu; Mohan, Kakita Veera; Kantam, Mannepalli Lakshmi; Likhar, Pravin R. Advanced Synthesis and Catalysis, 2013 , vol. 355, # 4 p. 751 - 756]

Ag-mediated reactions: Coupling and heterocyclization reactions

[Ahmed, Mohamed S. Mohamed; Sekiguchi, Akitoshi; Shimada, Tomohiro; Kawashima, Jun; Mori, Atsunori Bulletin of the Chemical Society of Japan, 2005 , vol. 78, # 2 p. 327 - 330]

Synthesis of unsymmetrically disubstituted ethynes by the palladium/copper (I)-cocatalyzed sila-Sonogashira–Hagihara coupling reactions of alkynylsilanes with aryl …

[Nishihara, Yasushi; Inoue, Eiji; Noyori, Shintaro; Ogawa, Daisuke; Okada, Yoshiaki; Iwasaki, Masayuki; Takagi, Kentaro Tetrahedron, 2012 , vol. 68, # 24 p. 4869 - 4881]

Ligand-free palladium-catalyzed decarboxylative coupling reactions of aryl iodides and alkynyl carboxylic acids

[Pyo, Ayoung; Kim, Ji Dang; Choi, Hyun Chul; Lee, Sunwoo Journal of Organometallic Chemistry, 2013 , vol. 724, p. 271 - 274]

Synthesis of unsymmetrically disubstituted ethynes by the palladium/copper (I)-cocatalyzed sila-Sonogashira–Hagihara coupling reactions of alkynylsilanes with aryl …

[Nishihara, Yasushi; Inoue, Eiji; Noyori, Shintaro; Ogawa, Daisuke; Okada, Yoshiaki; Iwasaki, Masayuki; Takagi, Kentaro Tetrahedron, 2012 , vol. 68, # 24 p. 4869 - 4881]

More Articles...