Journal article

Publication year: 2022

Journal: Chemistry - A European Journal

Volume number: 28

Issue number: 32

ISSN: 0947-6539

eISSN: 1521-3765

Open access status: Hybrid

DOI Link: https://doi.org/10.1002/chem.202200470

Publisher: Wiley

Abstract: 
We herein report a novel method for the coupling of unactivated alkynes and arylallenes, which relies on an unprecedented and regioselective 1,2-carboboration of the allene by an alkenylborane. The alkenylborane is conveniently prepared in situ by hydroboration of an alkyne with Piers' borane, i. e., HB(C6F5)(2). The boryl-substituted 1,4-dienes that are formed by this carboboration are well-suited for a subsequent Suzuki-Miyaura coupling with aryl iodides. This allowed us to develop a three-step, one-pot protocol for the synthesis of aryl-substituted 1,4-dienes. The generality of the reaction was demonstrated by the synthesis of twenty dienes with modular variations of all three reaction partners. The mechanism of the new 1,2-carboboration was investigated using dispersion corrected double-hybrid DFT computations that allowed us to rationalize the chemo- and regioselectivity of this key step.

Harvard Citation style: Averdunk, A., Hasenbeck, M., Mueller, T., Becker, J. and Gellrich, U. (2022) 1,2-Carboboration of Arylallenes by In Situ Generated Alkenylboranes for the Synthesis of 1,4-Dienes, Chemistry - A European Journal, 28(32), Article e202200470. https://doi.org/10.1002/chem.202200470

APA Citation style: Averdunk, A., Hasenbeck, M., Mueller, T., Becker, J., & Gellrich, U. (2022). 1,2-Carboboration of Arylallenes by In Situ Generated Alkenylboranes for the Synthesis of 1,4-Dienes. Chemistry - A European Journal. 28(32), Article e202200470. https://doi.org/10.1002/chem.202200470