Ortho lithiation-in situ borylation of substituted morpholine benzamides

Research output: Contribution to journal › Journal article › Research › peer-review

Standard

Ortho lithiation-in situ borylation of substituted morpholine benzamides. / Cederbalk, Anna; Lysén, Morten; Kehler, Jan; Kristensen, Jesper L.

In: Tetrahedron, Vol. 73, No. 12, 23.03.2017, p. 1576–1582.

Research output: Contribution to journal › Journal article › Research › peer-review

Harvard

Cederbalk, A, Lysén, M, Kehler, J & Kristensen, JL 2017, 'Ortho lithiation-in situ borylation of substituted morpholine benzamides', Tetrahedron, vol. 73, no. 12, pp. 1576–1582. https://doi.org/10.1016/j.tet.2017.02.002

APA

Cederbalk, A., Lysén, M., Kehler, J., & Kristensen, J. L. (2017). Ortho lithiation-in situ borylation of substituted morpholine benzamides. Tetrahedron, 73(12), 1576–1582. https://doi.org/10.1016/j.tet.2017.02.002

Vancouver

Cederbalk A, Lysén M, Kehler J, Kristensen JL. Ortho lithiation-in situ borylation of substituted morpholine benzamides. Tetrahedron. 2017 Mar 23;73(12):1576–1582. https://doi.org/10.1016/j.tet.2017.02.002

Author

Cederbalk, Anna ; Lysén, Morten ; Kehler, Jan ; Kristensen, Jesper L. / Ortho lithiation-in situ borylation of substituted morpholine benzamides. In: Tetrahedron. 2017 ; Vol. 73, No. 12. pp. 1576–1582.

Bibtex

@article{d7d2e103376d4f7f985809488ea4c11e,
title = "Ortho lithiation-in situ borylation of substituted morpholine benzamides",
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.",
keywords = "Borylation, Cross coupling, In-situ trapping, Lithiation, Selectivity",
author = "Anna Cederbalk and Morten Lys{\'e}n and Jan Kehler and Kristensen, {Jesper L.}",
year = "2017",
month = mar,
day = "23",
doi = "10.1016/j.tet.2017.02.002",
language = "English",
volume = "73",
pages = "1576–1582",
journal = "Tetrahedron",
issn = "0040-4020",
publisher = "Pergamon Press",
number = "12",

}

RIS

TY - JOUR

T1 - Ortho lithiation-in situ borylation of substituted morpholine benzamides

AU - Cederbalk, Anna

AU - Lysén, Morten

AU - Kehler, Jan

AU - Kristensen, Jesper L.

PY - 2017/3/23

Y1 - 2017/3/23

N2 - 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.

AB - 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.

KW - Borylation

KW - Cross coupling

KW - In-situ trapping

KW - Lithiation

KW - Selectivity

UR - http://www.scopus.com/inward/record.url?scp=85011957087&partnerID=8YFLogxK

U2 - 10.1016/j.tet.2017.02.002

DO - 10.1016/j.tet.2017.02.002

M3 - Journal article

AN - SCOPUS:85011957087

VL - 73

SP - 1576

EP - 1582

JO - Tetrahedron

JF - Tetrahedron

SN - 0040-4020

IS - 12

ER -

ID: 173700828