Dihydridoboranes: Selective Reagents for Hydroboration and Hydrodefluorination

Nicholas A Phillips; James O'Hanlon; Thomas N Hooper; Andrew J P White; Mark R Crimmin

doi:10.1021/acs.orglett.9b02515

Dihydridoboranes: Selective Reagents for Hydroboration and Hydrodefluorination

Org Lett. 2019 Sep 20;21(18):7289-7293. doi: 10.1021/acs.orglett.9b02515. Epub 2019 Sep 9.

Authors

Nicholas A Phillips¹, James O'Hanlon¹, Thomas N Hooper¹, Andrew J P White¹, Mark R Crimmin¹

Affiliation

¹ Department of Chemistry, Molecular Sciences Research Hub , Imperial College London , White City , London W12 0BZ , U.K.

PMID: 31497960
DOI: 10.1021/acs.orglett.9b02515

Abstract

The preparation of a new series of dihydridoboranes supported by N,N-chelating ligands, [R₂NCH₂CH₂NAr]^- (R = alkyl, Ar = aryl), is reported. These new boranes react selectively with carbonyls, imines, and a series of electron-deficient fluoroarenes. The reactivity is complementary to recognized reagents such as pinacolborane, catecholborane, NHC-BH₃, and borane (BH₃) itself. Selectivities are rationalized by invoking both open- and closed-chain forms of the reagents as part of equilibrium mixtures.