Application of vinyl tris(trimethylsilyl)germanes in Pd-catalyzed couplings |
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Authors: | Wang Zhizhong Wnuk Stanislaw F |
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Affiliation: | Department of Chemistry and Biochemistry, Florida International University, Miami, FL 33199, USA. |
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Abstract: | The oxidative treatment of vinyltris(trimethylsilyl)germanes with hydrogen peroxide (NaOH/H(2)O/THF) or tert-butyl peroxide (KH/THF) generates reactive germanol or germanoxane species that undergo Pd-catalyzed cross-couplings with aryl and alkenyl halides and aryl triflates in the presence of Pd(PPh(3))(4). Vinylgermanes having either a conjugated or isolated double bond serve as versatile transmetalation reagents. The E-germanes undergo coupling with retention of stereochemistry under aqueous and anhydrous conditions, while coupling of Z-germanes occurs with less stereoselectivity to produce a mixture of E/Z products. |
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