Stereocontrolled Formation of Styrenes by Pd(0)-catalyzed Cross-coupling of Photoactivated (E)-Alkenylgermanes with Aryl Bromides

The stereocontrolled synthesis of (E)-configured styrenes via Pd(0)-catalyzed cross-couping of (E)-alkenylgermanes with aryl bromides is described. The germanes employed have bis(naphthalen-2-ylmethyl) substitution to allow photooxidative activation toward coupling and a C8F17-fluorous tag to facili...

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Bibliographic Details
Published inChemistry letters Vol. 40; no. 9; pp. 995 - 997
Main Authors Tseng, Chih-Chung, Li, Mungyuen, Mo, Bingli, Warren, Sarah A., Spivey, Alan C.
Format Journal Article
LanguageEnglish
Published OXFORD Oxford Univ Press 05.09.2011
Subjects
Chemistry
Chemistry, Multidisciplinary
Physical Sciences
Science & Technology
DIAZONIUM SALTS
SOLID-PHASE SYNTHESIS
COMPLEXES
ARYLATION
BIARYL SYNTHESIS
ITERATIVE SYNTHESIS
ALKENYLSILANES
CINE SUBSTITUTION
TRIS(TRIMETHYLSILYL)GERMANES
TRANSITION-METALS
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Summary:The stereocontrolled synthesis of (E)-configured styrenes via Pd(0)-catalyzed cross-couping of (E)-alkenylgermanes with aryl bromides is described. The germanes employed have bis(naphthalen-2-ylmethyl) substitution to allow photooxidative activation toward coupling and a C8F17-fluorous tag to facilitate purification by fluorous solid-phase extraction (F-SPE). The selectivities obtained suggest that a germyl-Stille rather than Heck-type mechanism predominates in the coupling step.
Bibliography:researchfish
UKRI
ISSN:0366-7022
1348-0715
DOI:10.1246/cl.2011.995