Rhodium-Catalyzed Dehydrogenative Borylation of Aliphatic Terminal Alkenes with Pinacolborane

Masao Morimoto; Tomoya Miura; Masahiro Murakami

doi:10.1002/anie.201506328

Rhodium-Catalyzed Dehydrogenative Borylation of Aliphatic Terminal Alkenes with Pinacolborane

Angew Chem Int Ed Engl. 2015 Oct 19;54(43):12659-63. doi: 10.1002/anie.201506328. Epub 2015 Sep 2.

Authors

Masao Morimoto¹, Tomoya Miura², Masahiro Murakami³

Affiliations

¹ Department of Synthetic Chemistry and Biological Chemistry, Kyoto University, Katsura, Kyoto 615-8510 (Japan).
² Department of Synthetic Chemistry and Biological Chemistry, Kyoto University, Katsura, Kyoto 615-8510 (Japan). tmiura@sbchem.kyoto-u.ac.jp.
³ Department of Synthetic Chemistry and Biological Chemistry, Kyoto University, Katsura, Kyoto 615-8510 (Japan). murakami@sbchem.kyoto-u.ac.jp.

PMID: 26332866
DOI: 10.1002/anie.201506328

Abstract

Aliphatic terminal alkenes react with pinacolborane at ambient temperature to afford dehydrogenative borylation compounds as the major product when iPr-Foxap is used as the ligand with cationic rhodium(I) in the presence of norbornene, which acts as the sacrificial hydrogen acceptor. The reaction is applied to the one-pot syntheses of aldehydes and homoallylic alcohols from aliphatic terminal alkenes.

Keywords: alkenes; boron; reaction mechanisms; rhodium; synthetic methods.