Concept

Acetylide

Related publications (53)

Gold-Catalyzed Alkynylation: Acetylene-Transfer instead of Functionalization

Over the last fifteen years, gold has been raised from the status of an inert noble metal to one of the most-often-used catalysts in synthetic chemistry. The functionalization of the triple bond of alkynes has been especially successful in this respect. In ...

Wiley-V C H Verlag Gmbh2013

Synthesis of 1-[(Triisopropylsilyl)ethynyl]-1 lambda(3),2-benziodoxol-3(1H)-one and Alkynylation of Indoles, Thiophenes, and Anilines

Jérôme Waser, Jonathan Brand

An efficient procedure was developed for the synthesis of 1-[(triisopropylsilyl)ethynyl]-1 lambda(3),2-benziodoxol-3(1H)-one on a 100-mmol (36-g) scale. The benziodoxolone can be used for the gold-catalyzed direct alkynylation of indole, 2-hexylthiophene, ...

2012

Electrophilic alkynylation: the dark side of acetylene chemistry

Jérôme Waser, Jonathan Brand

In addition to the well-established nucleophilic alkynylation, the use of electrophilic alkynes can expand tremendously the scope of acetylene transfer reactions. The use of metal catalysis has recently led to a rebirth of this research area. Halogenoalkyn ...

Royal Society of Chemistry2012

Para-Selective Gold-Catalyzed Direct Alkynylation of Anilines

Jérôme Waser, Jonathan Brand

A method for the para-selective alkynylation of anilines is reported using AuCl as catalyst and triisopropylsilylethynyl-1,2-benziodoxol-3(1H)-one (TIPS-EBX) as an electrophilic acetylene equivalent. Para-alkynyl anilines substituted at positions 2 or 3 we ...

American Chemical Society2012

Ethynyl Benziodoxolones for the Direct Alkynylation of Heterocycles: Structural Requirement, Improved Procedure for Pyrroles, and Insights into the Mechanism

Rosario Scopelliti, Jérôme Waser, Jonathan Brand

This report describes a full study of the gold-catalyzed direct alkynylation of indoles, pyrroles, and thiophenes using alkynyl hypervalent iodine reagents, especially the study of the structural requirements of alkynyl benziodoxolones for an efficient ace ...

2012

Development of Catalytic Umpolung

Jonathan Brand

The development of efficient synthetic methodologies is crucial to access complex molecules in an economic, eco-friendly and safe way. The reversal of the intrinsic reactivity of functional groups, called Umpolung, allows alternative synthetic strategies a ...

EPFL2012

New Acetylene Chemistry

Davinia Fernández González

This thesis is divided in seven main chapters including an introduction about the state of the art in the field, four main chapters describing the main part of the work, a short insight on the implications of the presented results for other research projec ...

EPFL2011

Benziodoxole-based hypervalent iodine reagents for atom-transfer reactions

Jérôme Waser, Stefano Nicolai, Jonathan Brand, Davinia Fernández González

In the last decades, hypervalent iodine reagents have raised from chemical curiosities to mainstream reagents in organic synthesis. The use of benziodoxole-derived reagents has been especially successful in oxidation methods, whereas non-cyclic iodinanes h ...

2011

Benziodoxole-based hypervalent iodine reagents for atom-transfer reactions

Jérôme Waser, Stefano Nicolai, Jonathan Brand

2011

Palladium Alkynyl and Allenylidene Complexes: Very Efficient Precatalysts for C-C Coupling Reactions

Oxidative addition of BrC CC(=O)O-menthyl (1a) to [Pd(PPh3)(4)] affords the alkynyl complex trans-[Br(PPh3)(2)Pd-C CC(=O)O-menthyl] (2a). Subsequent reaction of 2a with trifluoroacetate gives trans-[(F3CCOO)(PPh3)(2)Pd-C CC(=O)O-menthyl] (3a). Reaction of ...

2011

Graph Chatbot

Chat with Graph Search

Ask any question about EPFL courses, lectures, exercises, research, news, etc. or try the example questions below.

DISCLAIMER: The Graph Chatbot is not programmed to provide explicit or categorical answers to your questions. Rather, it transforms your questions into API requests that are distributed across the various IT services officially administered by EPFL. Its purpose is solely to collect and recommend relevant references to content that you can explore to help you answer your questions.