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Alternating Radical Stabilities: A Convergent Route to Terminal and Internal Boronates
Author(s) -
Huang Qi,
Michalland Jean,
Zard Samir Z.
Publication year - 2019
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201906497
Subject(s) - moiety , pinacol , boron , chemistry , diethanolamine , stereochemistry , modular design , organic chemistry , computer science , catalysis , operating system
Pinacolato boronates (Bpin) with an empty p‐orbital on boron stabilize an adjacent carbon radical, in contrast to diethanolamino boronates [B(DEA)] where the boron is sp 3 ‐hybridized. By alternately placing a pinacol or diethanolamine moiety on the boron atom, thus stabilizing or not stabilizing the corresponding adjacent radical, it is possible to control the behavior of α‐boronyl xanthates and construct a large variety of terminal or internal boronates in a modular fashion. The remarkable tolerance of polar groups and the ability to introduce quaternary centers are particularly noteworthy features of this process.