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Issue 9, 2014
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Selective synthesis of secondary benzylic (Z)-allylboronates by Fe-catalyzed 1,4-hydroboration of 1-aryl-substituted 1,3-dienes

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Abstract

We have prepared and characterized a series of new iminopyridine iron complexes with a bulky diphenylphosphinomethyl-ketimine substituent. Using one of these iron complexes as the precatalyst, the hydroboration of 1-substituted 1,3-dienes containing aromatic groups with pinacolborane occurs regio- and stereoselectively to form secondary (Z)-allylboronates. In addition, we report the first examples of Suzuki–Miyaura cross-coupling of secondary allylboronates with aryl bromides. The reactions catalyzed by Pd(dba)2/Ad2PnBu yield the coupling products with excellent regioselectivity (γ/α > 99 : 1) and E-selectivity of the olefin geometry (E/Z > 99 : 1).

Graphical abstract: Selective synthesis of secondary benzylic (Z)-allylboronates by Fe-catalyzed 1,4-hydroboration of 1-aryl-substituted 1,3-dienes

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Article information


Submitted
22 Jul 2014
Accepted
05 Sep 2014
First published
23 Sep 2014

Org. Chem. Front., 2014,1, 1101-1106
Article type
Research Article

Selective synthesis of secondary benzylic (Z)-allylboronates by Fe-catalyzed 1,4-hydroboration of 1-aryl-substituted 1,3-dienes

Y. Cao, Y. Zhang, L. Zhang, D. Zhang, X. Leng and Z. Huang, Org. Chem. Front., 2014, 1, 1101
DOI: 10.1039/C4QO00206G

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