Standard

Convenient, DBU-promoted anti-Markovnikov hydration of 2-methyl-1-(3-arylprop-2-yn-1-yl)-1H-imidazoles in wet NMP. / Lukin, Alexei; Nichugovskaya, Anna; Vinogradova, Lyubov; Komarova, Kristina; Balalaie, Saeed; Dar'in, Dmitry; Krasavin, Mikhail.

In: Mendeleev Communications, Vol. 33, No. 4, 01.07.2023, p. 455-457.

Research output: Contribution to journal › Article › peer-review

Harvard

Lukin, A, Nichugovskaya, A, Vinogradova, L, Komarova, K, Balalaie, S, Dar'in, D & Krasavin, M 2023, 'Convenient, DBU-promoted anti-Markovnikov hydration of 2-methyl-1-(3-arylprop-2-yn-1-yl)-1H-imidazoles in wet NMP', Mendeleev Communications, vol. 33, no. 4, pp. 455-457. https://doi.org/10.1016/j.mencom.2023.06.004, https://doi.org/10.1016/j.mencom.2023.06.004

APA

Lukin, A., Nichugovskaya, A., Vinogradova, L., Komarova, K., Balalaie, S., Dar'in, D., & Krasavin, M. (2023). Convenient, DBU-promoted anti-Markovnikov hydration of 2-methyl-1-(3-arylprop-2-yn-1-yl)-1H-imidazoles in wet NMP. Mendeleev Communications, 33(4), 455-457. https://doi.org/10.1016/j.mencom.2023.06.004, https://doi.org/10.1016/j.mencom.2023.06.004

Vancouver

Lukin A, Nichugovskaya A, Vinogradova L, Komarova K, Balalaie S, Dar'in D et al. Convenient, DBU-promoted anti-Markovnikov hydration of 2-methyl-1-(3-arylprop-2-yn-1-yl)-1H-imidazoles in wet NMP. Mendeleev Communications. 2023 Jul 1;33(4):455-457. https://doi.org/10.1016/j.mencom.2023.06.004, https://doi.org/10.1016/j.mencom.2023.06.004

Author

Lukin, Alexei ; Nichugovskaya, Anna ; Vinogradova, Lyubov ; Komarova, Kristina ; Balalaie, Saeed ; Dar'in, Dmitry ; Krasavin, Mikhail. / Convenient, DBU-promoted anti-Markovnikov hydration of 2-methyl-1-(3-arylprop-2-yn-1-yl)-1H-imidazoles in wet NMP. In: Mendeleev Communications. 2023 ; Vol. 33, No. 4. pp. 455-457.

BibTeX

@article{a39ba76bfa2b42b59fe96aeb9a77415d,
title = "Convenient, DBU-promoted anti-Markovnikov hydration of 2-methyl-1-(3-arylprop-2-yn-1-yl)-1H-imidazoles in wet NMP",
abstract = "During attempts to involve 5-methyl-2-phenyl-1-(3-phenyl-prop-2-yn-1-yl)-1H-imidazole in a base-promoted, allene-mediated cyclization of the alkyne moiety onto the nearby aromatic ring, substantial amount of the ketone resulting from hydration of the alkyne with adventitious water was discovered. The formation of the ketone of the anti-Markovnikov alkyne hydration was developed into apreparative method. This method, alternative to the common acid- and metal-catalyzed approaches, may be of particular utility when alkyne hydration needs to be performed in the presence of acid-labile groups.",
keywords = "1,8-diazabicyclo[5.4.0]undec-7-ene, alkynes, anti-Markovnikov, hydration, imidazoles, propargylic amines",
author = "Alexei Lukin and Anna Nichugovskaya and Lyubov Vinogradova and Kristina Komarova and Saeed Balalaie and Dmitry Dar'in and Mikhail Krasavin",
year = "2023",
month = jul,
day = "1",
doi = "10.1016/j.mencom.2023.06.004",
language = "English",
volume = "33",
pages = "455--457",
journal = "Mendeleev Communications",
issn = "0959-9436",
publisher = "Elsevier",
number = "4",

}

RIS

TY - JOUR

T1 - Convenient, DBU-promoted anti-Markovnikov hydration of 2-methyl-1-(3-arylprop-2-yn-1-yl)-1H-imidazoles in wet NMP

AU - Lukin, Alexei

AU - Nichugovskaya, Anna

AU - Vinogradova, Lyubov

AU - Komarova, Kristina

AU - Balalaie, Saeed

AU - Dar'in, Dmitry

AU - Krasavin, Mikhail

PY - 2023/7/1

Y1 - 2023/7/1

N2 - During attempts to involve 5-methyl-2-phenyl-1-(3-phenyl-prop-2-yn-1-yl)-1H-imidazole in a base-promoted, allene-mediated cyclization of the alkyne moiety onto the nearby aromatic ring, substantial amount of the ketone resulting from hydration of the alkyne with adventitious water was discovered. The formation of the ketone of the anti-Markovnikov alkyne hydration was developed into apreparative method. This method, alternative to the common acid- and metal-catalyzed approaches, may be of particular utility when alkyne hydration needs to be performed in the presence of acid-labile groups.

AB - During attempts to involve 5-methyl-2-phenyl-1-(3-phenyl-prop-2-yn-1-yl)-1H-imidazole in a base-promoted, allene-mediated cyclization of the alkyne moiety onto the nearby aromatic ring, substantial amount of the ketone resulting from hydration of the alkyne with adventitious water was discovered. The formation of the ketone of the anti-Markovnikov alkyne hydration was developed into apreparative method. This method, alternative to the common acid- and metal-catalyzed approaches, may be of particular utility when alkyne hydration needs to be performed in the presence of acid-labile groups.

KW - 1,8-diazabicyclo[5.4.0]undec-7-ene

KW - alkynes

KW - anti-Markovnikov

KW - hydration

KW - imidazoles

KW - propargylic amines

UR - https://www.mendeley.com/catalogue/a0c16f70-b7e0-3d07-9c44-6db86f6df262/

U2 - 10.1016/j.mencom.2023.06.004

DO - 10.1016/j.mencom.2023.06.004

M3 - Article

VL - 33

SP - 455

EP - 457

JO - Mendeleev Communications

JF - Mendeleev Communications

SN - 0959-9436

IS - 4

ER -

ID: 113685953