Synthesis 2018; 50(16): 3149-3160
DOI: 10.1055/s-0036-1592004
special topic
© Georg Thieme Verlag Stuttgart · New York

One-Pot Preparation of Stable Organoboronate Reagents for the Functionalization of Unsaturated Four- and Five-Membered Carbo­- and Heterocycles

Andreas N. Baumann
University Ludwig-Maximilians, Department of Chemistry and Pharmacy, Butenandtstraße 5-13, 81377 Munich, Germany   Email: dorian.didier@cup.uni-muenchen.de
,
Michael Eisold
University Ludwig-Maximilians, Department of Chemistry and Pharmacy, Butenandtstraße 5-13, 81377 Munich, Germany   Email: dorian.didier@cup.uni-muenchen.de
,
Arif Music
University Ludwig-Maximilians, Department of Chemistry and Pharmacy, Butenandtstraße 5-13, 81377 Munich, Germany   Email: dorian.didier@cup.uni-muenchen.de
,
University Ludwig-Maximilians, Department of Chemistry and Pharmacy, Butenandtstraße 5-13, 81377 Munich, Germany   Email: dorian.didier@cup.uni-muenchen.de
› Author Affiliations
A.N.B., M.E., A.M. and D.D. are grateful to the Fonds der Chemischen Industrie, the Deutsche Forschungsgemeinschaft (DFG grant: DI 2227/2-1) and the SFB749 for Ph.D. funding and financial support.

Further Information

Publication History

Received: 23 February 2018

Accepted after revision: 03 April 2018

Publication Date:
14 May 2018 (eFirst)

These authors contributed equally to this work.

Published as part of the Special Topic Modern Coupling Approaches and their Strategic Applications in Synthesis

Abstract

Combining a facile preparation of organoboronates with their remarkable stability and functional group tolerance allows for the straightforward synthesis of four- and five-membered carbo- and hetero­cycles. While most strategies rely on the ex situ preparation of boronic acids as isolated intermediates, we demonstrate that in situ transmetalation of sensitive organometallics with boron alkoxides can lead to great stabilization of such species at room temperature. A considerable extension of the library of unsaturated strained structures is achieved through these sequences, expanding the potential applicability of such unusual building blocks.

Supporting Information

 
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