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Prof. Dr. Kazuhiko Semba, Prof. Dr. Tetsuaki Fujihara, Prof. Dr. Jun Terao and Prof. Dr. Yasushi Tsuji Copper-Catalyzed Borylation of α-Alkoxy Allenes with Bis(pinacolato)diboron: Efficient Synthesis of 2-Boryl 1,3-Butadienes Angewandte Chemie International Edition 52

Article first published online: 2 OCT 2013 | DOI: 10.1002/anie.201306843

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Something solid to build on: 2-Boryl 1,3-butadienes with various substitution patterns were formed in good to high yields in a copper-catalyzed borylation of α-alkoxy allenes with bis(pinacolato)diboron (see scheme; Bn=benzyl, pin=pinacolate, L is an N-heterocyclic carbene ligand). The products were found to be useful intermediates for the synthesis of cyclic vinyl boranes, α,β-unsaturated ketones, and functionalized multisubstituted dienes.

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