Ortho lithiation-in situ borylation of substituted morpholine benzamides

Research output: Contribution to journalJournal articleResearchpeer-review

Anna Cederbalk, Morten Lysén, Jan Kehler, Jesper L. Kristensen

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.

Original languageEnglish
JournalTetrahedron
Volume73
Issue number12
Pages (from-to)1576–1582
Number of pages7
ISSN0040-4020
DOIs
Publication statusPublished - 23 Mar 2017

    Research areas

  • Borylation, Cross coupling, In-situ trapping, Lithiation, Selectivity

ID: 173700828