Selective Synthesis of Tetrasubstituted Olefins by Copper-Mediated Acetoxythiolation of Internal Alkynes: Scope and Mechanistic Studies

2018 ◽  
Vol 24 (50) ◽  
pp. 13124-13135 ◽  
Author(s):  
Pedro Villuendas ◽  
Sara Ruiz ◽  
Pietro Vidossich ◽  
Agustí Lledós ◽  
Esteban P. Urriolabeitia
Keyword(s):  
Selective Synthesis ◽  
Mechanistic Studies ◽  
Internal Alkynes ◽  
Tetrasubstituted Olefins

Gold-catalyzed synthesis of N,O-heterocycles

2010 ◽  
Vol 82 (3) ◽  
pp. 657-668 ◽  
Author(s):  
A. Stephen K. Hashmi
Keyword(s):  
Double Bond ◽  
Gold Catalysis ◽  
Selective Synthesis ◽  
Mechanistic Studies ◽  
Nmr Studies ◽  
Internal Alkynes ◽  
Chelate Ligands ◽  
In Situ Nmr

The selective synthesis of oxazoles, alkylidene oxazoles, and 1,3-oxazines from N-propargyl carboxamides by choosing gold(III) or gold(I) catalysts and selecting terminal or internal alkynes as substrates is discussed. The mechanistic studies based on labeling experiments and intensive in situ NMR studies indicate an anti-oxyauration step and a proto-deauration with retention of the sterical arrangement at the double bond. The synthetic scope for gold(I) catalysts is very broad, allowing selective conversions to products with properties of chelate ligands, reactions of bromoarenes and the formation of acceptor-substituted oxazoles. With N-heterocyclic carbene (NHC) ligands in the presence of a base, even the vinylgold intermediates of the reactions leading to 1,3-oxazines could be isolated, a reaction with a great potential for future mechanistic studies and future applications of gold catalysis.

scholarly journals [3 + 2]-Cycloaddition reaction of sydnones with alkynes

2018 ◽  
Vol 14 ◽  
pp. 1317-1348 ◽  
Author(s):  
Veronika Hladíková ◽  
Jiří Váňa ◽  
Jiří Hanusek
Keyword(s):  
Reaction Rate ◽  
Cycloaddition Reaction ◽  
Mechanistic Studies ◽  
Reaction Conditions ◽  
Internal Alkynes

This review covers all known examples of [3 + 2]-cycloaddition between sydnones and both terminal as well as internal alkynes/cycloalkynes taken from literature since its discovery by Huisgen in 1962 up to the current date. Except enumeration of synthetic applications it also covers mechanistic studies, catalysis, effects of substituents and reaction conditions influencing reaction rate and regioselectivity.

Photoinduced Oxidative Cross-Coupling for O–S Bond Formation: A Facile Synthesis of Alkyl Benzenesulfonates

Synlett ◽  
2017 ◽  
Vol 28 (13) ◽  
pp. 1558-1563 ◽  
Author(s):  
Aiwen Lei ◽  
Atul Singh ◽  
Hong Yi ◽  
Guoting Zhang ◽  
Changliang Bian ◽  
...  
Keyword(s):  
Visible Light ◽  
Bond Formation ◽  
Cross Coupling ◽  
Selective Synthesis ◽  
Mechanistic Studies ◽  
Facile Synthesis ◽  
Metal Free

We have developed a photoinduced oxidative cross-coupling of thiophenols with alcohols for O–S bond formation. The protocol uses visible light, a metal-free photocatalyst, and oxygen as the oxidant for the selective synthesis of alkyl benzenesulfonates; no ligand co-additive is necessary. Mechanistic studies suggested that the disulfide and alkyl benzenesulfinate are involved as intermediates and that the transformation proceeds by a radical pathway.

ChemInform Abstract: Ruthenium-Catalyzed Oxidative Coupling of Primary Amines with Internal Alkynes Through C-H Bond Activation: Scope and Mechanistic Studies.

ChemInform ◽  
2015 ◽  
Vol 46 (39) ◽  
pp. no-no
Author(s):  
Sara Ruiz ◽  
Pedro Villuendas ◽  
Manuel A. Ortuno ◽  
Agusti Lledos ◽  
Esteban P. Urriolabeitia
Keyword(s):  
Oxidative Coupling ◽  
Bond Activation ◽  
Primary Amines ◽  
Mechanistic Studies ◽  
Internal Alkynes

Z ‐Selective Synthesis of α‐Sulfanyl Carbonyl Compounds from Internal Alkynes and Thiols via Photoredox Catalysis

2021 ◽  
Author(s):  
Alberto Luridiana ◽  
Angelo Frongia ◽  
Mariano Andrea Scorciapino ◽  
Giuliano Malloci ◽  
Barbara Manconi ◽  
...  
Keyword(s):  
Carbonyl Compounds ◽  
Selective Synthesis ◽  
Photoredox Catalysis ◽  
Internal Alkynes
Sign in / Sign up

Export Citation Format

Share Document