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- W2933266887 abstract "Abstract The flexible synthesis of tetra- and triarylethenes bearing different aryl groups has been a long-standing challenge in organic synthesis. Here we report a palladium-catalysed syn -diarylation of arylethynyl N -methyliminodiacetyl (MIDA) boronates. The products, triarylalkenyl N -methyliminodiacetyl boronates, allow a step-economic and modular synthesis of tetra- or triarylethenes via a subsequent stereospecific Suzuki-Miyaura coupling reaction or base-promoted protodeborylation, respectively. Use of the sp 3 -B(MIDA) masked aryl alkyne is the key factor for success by offering an exceptionally good regioselectivity for the boron-retentive coupling. The unusual regioselectivity is believed to arise from the stabilization due to the strong electron donation from the C−Pd σ bond to the p-orbital of boron in the transition state of migratory insertion. A broad range of differently substituted tetra- and triarylethenes are constructed in good yields and geometrical control. Synthetic manipulation of the C-B bond also enables the facile construction of several other types of tetra-substituted alkenes." @default.
- W2933266887 created "2019-04-11" @default.
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- W2933266887 date "2019-03-22" @default.
- W2933266887 modified "2023-10-06" @default.
- W2933266887 title "Regio- and stereoselective synthesis of tetra- and triarylethenes by N-methylimidodiacetyl boron-directed palladium-catalysed three-component coupling" @default.
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- W2933266887 doi "https://doi.org/10.1038/s42004-019-0137-0" @default.
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