Ortho lithiation-in situ borylation of substituted morpholine benzamides. Issue 12 (23rd March 2017)

• Record Type: Journal Article
• Authors: Cederbalk, Anna; Lysén, Morten; Kehler, Jan; Kristensen, Jesper L.
• Is Part Of: Tetrahedron. Volume 73:Issue 12(2017)
• Page Start: 1576
• Page End: 1582
• Publication Date: 2017-03-23
• Subjects: Lithiation -- In-situ trapping -- Borylation -- Selectivity -- Cross coupling; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tet.2017.02.002
• Languages: English
• ISSNs: 0040-4020

Abstract

Abstract: Morpholine amides are cheap and safe alternative to Weinreb amides as acylating agents of organometallic species. Herein, the in-situ lithiation/borylation of 18 ortho- meta- and para-substituted morpholine benzamides has been investigated. 10 of the 18 substrates provided the desired boronic esters as the major isomer (>90% regioselectivity) in crude isolated yields ranging from 68 to 93%. The synthetic usability of such building blocks was subsequently illustrated via the synthesis of a kinase inhibitor. Graphical abstract: