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Alternating Radical Stabilities: A Convergent Route to Terminal and Internal Boronates
Qi Huang1, Jean Michalland1, Samir Z Zard1
1Laboratoire de Synthèse Organique, CNRS UMR 7652, Ecole polytechnique, Route de Saclay, 91128, Palaiseau Cedex, France.
Abstract:
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 sp3 -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.
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