Radical instability in aid of efficiency: A powerful route to highly functional MIDA Boronates

Béatrice Quiclet-Sire; Samir Z. Zard

doi:10.1021/jacs.5b03893

Radical instability in aid of efficiency: A powerful route to highly functional MIDA Boronates

Béatrice Quiclet-Sire
, Samir Z. Zard

Laboratoire de Synthèse Organique

Research output: Contribution to journal › Article › peer-review

Abstract

The inability of the sp³ boron in MIDA boronates to stabilize an adjacent radical makes possible the efficient addition of a wide array of xanthates to vinyl MIDA boronate, leading to highly functionalized and diverse aliphatic organoboron structures. The lack of radical stabilization also allows the exchange of the xanthate in the adducts with a bromine. In one case, the bromine was substituted to generate a cyclopropyl MIDA derivative.

Original language	English
Pages (from-to)	6762-6765
Number of pages	4
Journal	Journal of the American Chemical Society
Volume	137
Issue number	21
DOIs	https://doi.org/10.1021/jacs.5b03893
Publication status	Published - 3 Jun 2015
Externally published	Yes

Access to Document

10.1021/jacs.5b03893

Cite this

@article{5734b1bcb47246b295db3c601cfb4e74,

title = "Radical instability in aid of efficiency: A powerful route to highly functional MIDA Boronates",

abstract = "The inability of the sp3 boron in MIDA boronates to stabilize an adjacent radical makes possible the efficient addition of a wide array of xanthates to vinyl MIDA boronate, leading to highly functionalized and diverse aliphatic organoboron structures. The lack of radical stabilization also allows the exchange of the xanthate in the adducts with a bromine. In one case, the bromine was substituted to generate a cyclopropyl MIDA derivative.",

author = "B{\'e}atrice Quiclet-Sire and Zard, \{Samir Z.\}",

note = "Publisher Copyright: {\textcopyright} 2015 American Chemical Society.",

year = "2015",

month = jun,

day = "3",

doi = "10.1021/jacs.5b03893",

language = "English",

volume = "137",

pages = "6762--6765",

journal = "Journal of the American Chemical Society",

issn = "0002-7863",

number = "21",

}

TY - JOUR

T1 - Radical instability in aid of efficiency

T2 - A powerful route to highly functional MIDA Boronates

AU - Quiclet-Sire, Béatrice

AU - Zard, Samir Z.

PY - 2015/6/3

Y1 - 2015/6/3

N2 - The inability of the sp3 boron in MIDA boronates to stabilize an adjacent radical makes possible the efficient addition of a wide array of xanthates to vinyl MIDA boronate, leading to highly functionalized and diverse aliphatic organoboron structures. The lack of radical stabilization also allows the exchange of the xanthate in the adducts with a bromine. In one case, the bromine was substituted to generate a cyclopropyl MIDA derivative.

AB - The inability of the sp3 boron in MIDA boronates to stabilize an adjacent radical makes possible the efficient addition of a wide array of xanthates to vinyl MIDA boronate, leading to highly functionalized and diverse aliphatic organoboron structures. The lack of radical stabilization also allows the exchange of the xanthate in the adducts with a bromine. In one case, the bromine was substituted to generate a cyclopropyl MIDA derivative.

UR - https://www.scopus.com/pages/publications/84930685403

U2 - 10.1021/jacs.5b03893

DO - 10.1021/jacs.5b03893

M3 - Article

C2 - 25984592

AN - SCOPUS:84930685403

SN - 0002-7863

VL - 137

SP - 6762

EP - 6765

JO - Journal of the American Chemical Society

JF - Journal of the American Chemical Society

IS - 21

ER -

Radical instability in aid of efficiency: A powerful route to highly functional MIDA Boronates

Abstract

Access to Document

Other files and links

Fingerprint

Cite this