Palladium-catalyzed C-glycosylation and annulation of o-alkynylanilines with 1-iodoglycals: convenient access to 3-indolyl-C-glycosides

2020 ◽  
Vol 18 (43) ◽  
pp. 8834-8838
Author(s):  
Jianchao Liu ◽  
Xiao Xiao ◽  
Puren Han ◽  
Huiwen Zhou ◽  
Qi-Shuang Yin ◽  
...  
Keyword(s):  
Practical Approach ◽  
Palladium Catalyzed ◽  
Convenient Access

An efficient and practical approach for the synthesis of 3-indolyl-C-glycosides through a palladium-catalyzed annulation/C-glycosylation sequence of o-alkynylanilines has been developed.

Palladium-catalyzed carbonylative transformation of aryl iodides and sulfonyl chlorides: convenient access to thioesters

2020 ◽  
Vol 7 (6) ◽  
pp. 885-889 ◽  
Author(s):  
Xinxin Qi ◽  
Zhi-Peng Bao ◽  
Xiao-Feng Wu
Keyword(s):  
Sulfonyl Chlorides ◽  
Aryl Iodides ◽  
Palladium Catalyzed ◽  
Convenient Access

A palladium-catalyzed carbonylative transformation of aryl iodides and sulfonyl chlorides to thioesters has been studied.

Synthesis of 2-Pyrrolidinones by Palladium-Catalyzed [3+2] Cycloaddition of Isocyanates

Synlett ◽  
2019 ◽  
Vol 30 (05) ◽  
pp. 581-585 ◽  
Author(s):  
Rolf Breinbauer ◽  
Marko Kljajic ◽  
Thomas Schlatzer
Keyword(s):  
Ring Closure ◽  
Olefin Isomerization ◽  
Stereogenic Centers ◽  
Palladium Catalyzed ◽  
Synthetic Equivalent ◽  
Mechanistic Investigations ◽  
Convenient Access

Pd/DPEphos catalyzes the [3+2] cycloaddition of various alkyl isocyanates with 2-acetoxymethyl-3-allyltrimethylsilane as a synthetic equivalent of trimethylenemethane (TMM). Taking advantage of 2-acetoxymethyl-3-allyltrimethylsilane acting both as nucleophile as well as electrophile this reaction gives a convenient access to 5-ring lactams with an exocyclic alkene moiety. The formation of the β,γ-unsaturated 2-pyrrolidinones occurs without olefin isomerization and without epimerization of the stereogenic centers. Mechanistic investigations suggest an initial N-allylation of the isocyanate followed by nucleophilic ring closure furnishing the desired 2-pyrrolidinones.

scholarly journals Optimised Conditions for the Palladium-Catalyzed Hydrogenolysis of Benzyl and Naphthylmethyl Ethers: Preventing Saturation of Aromatic Protecting Groups

2020 ◽  
Author(s):  
Conor Crawford ◽  
Stefan Oscarson
Keyword(s):  
Treatment Strategy ◽  
Continuous Flow ◽  
Practical Approach ◽  
Protecting Groups ◽  
Flow Conditions ◽  
Selective Catalyst ◽  
Palladium Catalyzed ◽  
Synthetic Oligosaccharides ◽  
Pre Treatment

<p>Whilst carrying out palladium catalysed hydrogenolysis to deprotect synthetic oligosaccharides, saturation of the benzyl and naphthylmethyl ether groups to their corresponding ether was observed. In order to suppress this unwanted hydrogenation, we report a scalable practical approach using a catalyst pre-treatment strategy, which is effective under batch or continuous flow conditions. This suppressed the unwanted hydrogenation side-products and created a selective catalyst for hydrogenolysis of benzyl and naphthylmethyl ethers. We demonstrate the efficient deprotection of a set of structurally diverse oligosaccharides (5 examples, >73%).</p>

scholarly journals Convenient Access to C10- and C11-(di)arylated dibenzo[b ,f ]azepines via Palladium-catalyzed C−H Bonds Cleavages

2018 ◽  
Vol 361 (4) ◽  
pp. 791-802 ◽  
Author(s):  
Haoran Li ◽  
Thierry Roisnel ◽  
Jean-François Soulé ◽  
Henri Doucet
Keyword(s):  
Palladium Catalyzed ◽  
Convenient Access

scholarly journals Optimised Conditions for the Palladium-Catalyzed Hydrogenolysis of Benzyl and Naphthylmethyl Ethers: Preventing Saturation of Aromatic Protecting Groups

2020 ◽  
Author(s):  
Conor Crawford ◽  
Stefan Oscarson
Keyword(s):  
Treatment Strategy ◽  
Continuous Flow ◽  
Practical Approach ◽  
Protecting Groups ◽  
Flow Conditions ◽  
Selective Catalyst ◽  
Palladium Catalyzed ◽  
Synthetic Oligosaccharides ◽  
Pre Treatment

<p>Whilst carrying out palladium catalysed hydrogenolysis to deprotect synthetic oligosaccharides, saturation of the benzyl and naphthylmethyl ether groups to their corresponding ether was observed. In order to suppress this unwanted hydrogenation, we report a scalable practical approach using a catalyst pre-treatment strategy, which is effective under batch or continuous flow conditions. This suppressed the unwanted hydrogenation side-products and created a selective catalyst for hydrogenolysis of benzyl and naphthylmethyl ethers. We demonstrate the efficient deprotection of a set of structurally diverse oligosaccharides (5 examples, >73%).</p>

Palladium-catalyzed synthesis of allylic thioacetates. A convenient access to allylic thiols

Tetrahedron ◽  
1999 ◽  
Vol 55 (14) ◽  
pp. 4369-4376 ◽  
Author(s):  
Sunil Divekar ◽  
Mohamed Safi ◽  
Mohamed Soufiaoui ◽  
Denis Sinou
Keyword(s):  
Palladium Catalyzed ◽  
Convenient Access
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