One-Pot Synthesis of Styrene Derivatives from Allyl Silanes via B(C6F5)3-Catalyzed Isomerization-Hiyama Coupling
Betty A. Kustiana, Rebecca L. Melen and Louis C. Morrill*
*Cardiff Catalysis Institute, School of Chemistry, Cardiff University, Main Building, Park Place, Cardiff CF10 3AT, U.K.,
Email: MorrillLC
cardiff.ac.uk
B. A. Kustiana, R. L. Melen, L. C. Morrill, Org. Lett., 2022, 24, 8694-8697.
DOI: 10.1021/acs.orglett.2c03584
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Abstract
A B(C6F5)3-catalyzed E-selective isomerization of readily accessible allyl silanes and subsequent Hiyama coupling of the versatile alkenyl silane intermediates provide a broad range of styrene derivatives.
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General procedure
In the glovebox under Ar, an oven-dried 10 mL microwave vial equipped with a magnetic stirrer bar was charged with B(C6F5)3 (5 mol %), allylbenzyldimethylsilane (0.1 mmol), and toluene (0.4 mL). The vial was sealed with an aluminium crimp cap and stirred at 140 °C for 48 h. It was cooled to rt, TBAF (2 equiv.) was added by syringe and stirred at rt for 10 min. The aluminium cap was removed, ArI (1 equiv.) and Pd(dba)2 (4 mol %) were added. The vial then was sealed with an aluminium crimp cap and stirred at 40-50 ˚C for 24 h. it was cooled to rt, wet toluene was added. Then 1,3,5-trimethylbenzene (0.1 mmol) was added and stirred for 5 min and the yield was analysed using 1H NMR. Purification was done by flask silica chromatography with the stated eluent: 100% PE for (E)-1-(phenoxymethyl)-4-(prop-1-en-1-yl)benzene, 20% EtOAc in PE for (E)-4-(prop-1-en-1-yl)benzonitrile.
Key Words
ID: J54-Y2022
