Selective Synthesis of Enol Ethers by Nickel-Catalyzed Cross Coupling of α-oxy Vinylsulfones with Alkylzinc Reagents

2021 ◽  
Author(s):  
Liang Gong ◽  
Qian Zhang ◽  
Demeng Xie ◽  
Wei Zhang ◽  
Shiyang Xu ◽  
...  
Keyword(s):  
Coupling Reaction ◽  
Cross Coupling ◽  
Selective Synthesis ◽  
Enol Ethers ◽  
Negishi Coupling

We describe here a Ni-catalyzed Negishi coupling reaction to prepare 1,2-dialkyl enol ethers in a stereoconvergent fashion. This method employs readily available and bench-stable α-oxy-vinylsulfones as electrophiles. The C–sulfone bond...

ChemInform Abstract: Selective Synthesis of Partially Protected Nonsymmetric Biphenols by Reagent- and Metal-Free Anodic Cross-Coupling Reaction.

ChemInform ◽  
2016 ◽  
Vol 47 (52) ◽  
Author(s):  
Anton Wiebe ◽  
Dieter Schollmeyer ◽  
Katrin M. Dyballa ◽  
Robert Franke ◽  
Siegfried R. Waldvogel
Keyword(s):  
Coupling Reaction ◽  
Cross Coupling ◽  
Selective Synthesis ◽  
Metal Free ◽  
Cross Coupling Reaction

Pd/C-catalyzed cross-coupling reaction of benzyloxysilanes with halosilanes for selective synthesis of unsymmetrical siloxanes

RSC Advances ◽  
2014 ◽  
Vol 4 (37) ◽  
pp. 19099 ◽  
Author(s):  
Masayasu Igarashi ◽  
Keiko Kubo ◽  
Tomohiro Matsumoto ◽  
Kazuhiko Sato ◽  
Wataru Ando ◽  
...  
Keyword(s):  
Coupling Reaction ◽  
Cross Coupling ◽  
Selective Synthesis ◽  
Cross Coupling Reaction

ChemInform Abstract: Pd/C-Catalyzed Cross-Coupling Reaction of Benzyloxysilanes with Halosilanes for Selective Synthesis of Unsymmetrical Siloxanes.

ChemInform ◽  
2014 ◽  
Vol 45 (51) ◽  
pp. no-no
Author(s):  
Masayasu Igarashi ◽  
Keiko Kubo ◽  
Tomohiro Matsumoto ◽  
Kazuhiko Sato ◽  
Wataru Ando ◽  
...  
Keyword(s):  
Coupling Reaction ◽  
Cross Coupling ◽  
Selective Synthesis ◽  
Cross Coupling Reaction

Routes to some 3,6-disubstituted phthalonitriles and examples of phthalocyanines derived therefrom: An overview

2013 ◽  
Vol 17 (08n09) ◽  
pp. 649-664 ◽  
Author(s):  
Martin J. Heeney ◽  
Shaya A. Al-Raqa ◽  
Aurélien Auger ◽  
Paul M. Burnham ◽  
Andrew N. Cammidge ◽  
...  
Keyword(s):  
Metal Ion ◽  
Near Infrared ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
Suzuki Coupling ◽  
Central Metal ◽  
Coupling Reactions ◽  
Negishi Coupling ◽  
Suzuki Coupling Reaction ◽  
Cross Coupling Reactions

The paper reviews a selection of synthetic pathways that provide access to 3,6-disubstituted phthalonitriles, precursors for the synthesis of 1,4,8,11,15,18,22,25-octasubstituted phthalocyanine derivatives. Early routes using Diels–Alder reactions for the synthesis of 3,6-dialkyl, 3,6-dialkoxymethyl, 3,6-dialkenyl and 3,6-diphenylphthalonitriles are appraised. However, the emphasis of the review focuses on the scope and applications of 2,3-dicyanohydroquinone as a starting material for obtaining 3,6-disubstituted phthalonitriles. The earliest example of the use of 2,3-dicyanohydroquinone concerned its O -alkylation to afford 3,6-dialkoxyphthalonitriles. These are immediate precursors to near-infrared absorbing phthalocyanine derivatives. Triflation of 2,3-dicyanohydroquinone extends the scope of the compound for phthalocyanine synthesis; the bis-triflate derivative is susceptible to S N Ar reactions and readily reacts with thiols to provide 3,6-bis(alkylsulfanyl) and 3,6-bis(arylsulfanyl)phthalonitriles. 3,6-Bis(phenylselenyl)phthalonitrile has also been obtained recently from the same precursor. Phthalocyanine derivatives obtained from them typically show a strongly bathochromically shifted Q-band absorption that is particularly sensitive to the central metal ion. The bis-triflate of 2,3-dicyanohydroquinone is also an ideal precursor for participation in cross-coupling reactions. Examples from the University of East Anglia group and elsewhere are presented which show the application of the nickel-catalyzed Negishi coupling reaction using alkylzinc halide derivatives. Yields of 3,6-dialkylphthalonitriles and 3,6-bis(substituted alkyl)phthalonitriles range from ca. 40 to 70%. Direct comparison for one example shows that the yield from the Negishi coupling method is higher than that using the Suzuki coupling protocol. Examples of the preparation of 3,6-diarylphthalonitriles from 2,3-dicyanohydroquinone bis-triflate using the Suzuki coupling reaction are reported with yields of the order of 65–70%. The review also includes a further application of 2,3-dicyanohydroquinone as a precursor to both monobromo and dibromo derivatives of 3,6-dibutoxyphthalonitrile. These compounds provide opportunities for cross-coupling at the brominated sites to provide more complex derivatives with the potential to serve as precursors of highly substituted phthalocyanine derivatives.

Highly Selective Synthesis of Hydrosiloxanes by Au-Catalyzed Dehydrogenative Cross-Coupling Reaction of Silanols with Hydrosilanes

ACS Catalysis ◽  
2017 ◽  
Vol 7 (3) ◽  
pp. 1836-1840 ◽  
Author(s):  
Yasushi Satoh ◽  
Masayasu Igarashi ◽  
Kazuhiko Sato ◽  
Shigeru Shimada
Keyword(s):  
Coupling Reaction ◽  
Cross Coupling ◽  
Selective Synthesis ◽  
Cross Coupling Reaction
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