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Reversible 1,1‐Hydroboration: Boryl Insertion into a CN Bond and Competitive Elimination of HBR 2 or RH
Author(s) -
Yang DengTao,
Mellerup Soren K.,
Wang Xiang,
Lu JiaSheng,
Wang Suning
Publication year - 2015
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201500487
Subject(s) - hydroboration , chemistry , boranes , molecule , adduct , stereochemistry , medicinal chemistry , reactivity (psychology) , organic chemistry , boron , catalysis , medicine , alternative medicine , pathology
Boranes with the general formula of HBR 2 have been found to undergo a facile 1,1‐hydroboration reaction with pyrido[1,2‐a]isoindole ( A ), resulting in insertion of a BR 2 unit into a CN bond and the formation of a variety of BN heterocycles. Investigation on the thermal reactivity of the BN heterocycles revealed that these molecules have two distinct and competitive thermal elimination pathways: HBR 2 elimination (or retro‐hydroboration) versus RH elimination, depending on the R group on the B atom and the chelate backbone. Mechanistic aspects of these highly unusual reactions have been established from both experimental and computational evidence. Adduct formation between HBR 2 and A was found to be the key intermediate in 1,1‐hydroboration of A .