Dihydridoboranes: Selective Reagents for Hydroboration and Hydrodefluorination

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 reag...

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Bibliographic Details
Published inOrganic letters Vol. 21; no. 18; pp. 7289 - 7293
Main Authors Phillips, Nicholas A, O’Hanlon, James, Hooper, Thomas N, White, Andrew J. P, Crimmin, Mark R
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 20.09.2019
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
BORANE
ALKENES
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Summary: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.
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ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.9b02515