Pd-catalyzed synthesis of 1-(hetero)aryl-2,2,2-trichloroethanols using chloral hydrate and (hetero)arylboroxines

1-(Hetero)aryl-2,2,2-trichloroethanols are useful key intermediates for the synthesis of various bioactive compounds. Herein, we describe N-heterocyclic carbene (NHC)-coordinated cyclometallated palladium complex (CYP)-catalyzed (hetero)aryl addition of chloral hydrate using (hetero)arylboroxines, p...

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Detalles Bibliográficos
Autores principales: Shimizu, Minori, Okuda, Yuta, Toyoda, Koki, Akiyama, Ryo, Shinozaki, Hiraku, Yamamoto, Tetsuya
Formato: Online Artículo Texto
Lenguaje:English
Publicado: The Royal Society of Chemistry 2021
Materias:
Chemistry
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9033206/
https://www.ncbi.nlm.nih.gov/pubmed/35480199
http://dx.doi.org/10.1039/d1ra02403e
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author Shimizu, Minori
Okuda, Yuta
Toyoda, Koki
Akiyama, Ryo
Shinozaki, Hiraku
Yamamoto, Tetsuya
author_facet Shimizu, Minori
Okuda, Yuta
Toyoda, Koki
Akiyama, Ryo
Shinozaki, Hiraku
Yamamoto, Tetsuya
author_sort Shimizu, Minori
collection PubMed
description 1-(Hetero)aryl-2,2,2-trichloroethanols are useful key intermediates for the synthesis of various bioactive compounds. Herein, we describe N-heterocyclic carbene (NHC)-coordinated cyclometallated palladium complex (CYP)-catalyzed (hetero)aryl addition of chloral hydrate using (hetero)arylboroxines, providing a new approach to 1-(hetero)aryl-2,2,2-trichloroethanols. Notably, PhS-IPent-CYP which coordinated the bulky yet flexible 2,6-di(pentan-3-yl)aniline (IPent)-based NHC showed good catalytic activities and promoted the transformation in 24–97% yields.
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spelling pubmed-90332062022-04-26 Pd-catalyzed synthesis of 1-(hetero)aryl-2,2,2-trichloroethanols using chloral hydrate and (hetero)arylboroxines Shimizu, Minori Okuda, Yuta Toyoda, Koki Akiyama, Ryo Shinozaki, Hiraku Yamamoto, Tetsuya RSC Adv Chemistry 1-(Hetero)aryl-2,2,2-trichloroethanols are useful key intermediates for the synthesis of various bioactive compounds. Herein, we describe N-heterocyclic carbene (NHC)-coordinated cyclometallated palladium complex (CYP)-catalyzed (hetero)aryl addition of chloral hydrate using (hetero)arylboroxines, providing a new approach to 1-(hetero)aryl-2,2,2-trichloroethanols. Notably, PhS-IPent-CYP which coordinated the bulky yet flexible 2,6-di(pentan-3-yl)aniline (IPent)-based NHC showed good catalytic activities and promoted the transformation in 24–97% yields. The Royal Society of Chemistry 2021-05-18 /pmc/articles/PMC9033206/ /pubmed/35480199 http://dx.doi.org/10.1039/d1ra02403e Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by-nc/3.0/
spellingShingle Chemistry
Shimizu, Minori
Okuda, Yuta
Toyoda, Koki
Akiyama, Ryo
Shinozaki, Hiraku
Yamamoto, Tetsuya
Pd-catalyzed synthesis of 1-(hetero)aryl-2,2,2-trichloroethanols using chloral hydrate and (hetero)arylboroxines
title Pd-catalyzed synthesis of 1-(hetero)aryl-2,2,2-trichloroethanols using chloral hydrate and (hetero)arylboroxines
title_full Pd-catalyzed synthesis of 1-(hetero)aryl-2,2,2-trichloroethanols using chloral hydrate and (hetero)arylboroxines
title_fullStr Pd-catalyzed synthesis of 1-(hetero)aryl-2,2,2-trichloroethanols using chloral hydrate and (hetero)arylboroxines
title_full_unstemmed Pd-catalyzed synthesis of 1-(hetero)aryl-2,2,2-trichloroethanols using chloral hydrate and (hetero)arylboroxines
title_short Pd-catalyzed synthesis of 1-(hetero)aryl-2,2,2-trichloroethanols using chloral hydrate and (hetero)arylboroxines
title_sort pd-catalyzed synthesis of 1-(hetero)aryl-2,2,2-trichloroethanols using chloral hydrate and (hetero)arylboroxines
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9033206/
https://www.ncbi.nlm.nih.gov/pubmed/35480199
http://dx.doi.org/10.1039/d1ra02403e
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