Synthesis

1-Methyl-1-vinyl-and 1-Methyl-1-(prop-2-enyl) silacyclobutane: Reagents for Palladium-Catalyzed Cross-Coupling Reactions of Aryl Halides

SE Denmark, Z Wang

Index: Denmark, Scott E.; Wang, Zhigang Synthesis, 2000 , # 7 p. 999 - 1003

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Citation Number: 50

Abstract

Abstract: 1-Methyl-1-vinylsilacyclobutane (1) and 1-methyl-1-(prop-2-enyl) silacyclobutane (2) undergo rapid and high yielding cross-coupling with aromatic halides. Many different substituents and patterns on the aromatic moiety are tolerated. All reactions can be run at room temperature and require the presence of tetrabutylammonium fluoride and Pd (dba) 2. Both silacyclobutanes can be made in one step from commercially available precursors. ...

~86%

~70%

~83%

~73%

~86%

~72%

~91%

~87%

~86%

~78%

~78%

~82%

~73%

~90%

~85%

~89%

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