Chemoselective Homologation–Deoxygenation Strategy Enabling the Direct Conversion of Carbonyls into (n+1)-Halomethyl-Alkanes

[Image: see text] The sequential installation of a carbenoid and a hydride into a carbonyl, furnishing halomethyl alkyl derivatives, is reported. Despite the employment of carbenoids as nucleophiles in reactions with carbon-centered electrophiles, sp(3)-type alkyl halides remain elusive materials fo...

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Autores principales: Miele, Margherita, Citarella, Andrea, Langer, Thierry, Urban, Ernst, Zehl, Martin, Holzer, Wolfgang, Ielo, Laura, Pace, Vittorio
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2020
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8011987/
https://www.ncbi.nlm.nih.gov/pubmed/32910659
http://dx.doi.org/10.1021/acs.orglett.0c02831
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author Miele, Margherita
Citarella, Andrea
Langer, Thierry
Urban, Ernst
Zehl, Martin
Holzer, Wolfgang
Ielo, Laura
Pace, Vittorio
author_facet Miele, Margherita
Citarella, Andrea
Langer, Thierry
Urban, Ernst
Zehl, Martin
Holzer, Wolfgang
Ielo, Laura
Pace, Vittorio
author_sort Miele, Margherita
collection PubMed
description [Image: see text] The sequential installation of a carbenoid and a hydride into a carbonyl, furnishing halomethyl alkyl derivatives, is reported. Despite the employment of carbenoids as nucleophiles in reactions with carbon-centered electrophiles, sp(3)-type alkyl halides remain elusive materials for selective one-carbon homologations. Our tactic levers on using carbonyls as starting materials and enables uniformly high yields and chemocontrol. The tactic is flexible and is not limited to carbenoids. Also, diverse carbanion-like species can act as nucleophiles, thus making it of general applicability.
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spelling pubmed-80119872021-04-02 Chemoselective Homologation–Deoxygenation Strategy Enabling the Direct Conversion of Carbonyls into (n+1)-Halomethyl-Alkanes Miele, Margherita Citarella, Andrea Langer, Thierry Urban, Ernst Zehl, Martin Holzer, Wolfgang Ielo, Laura Pace, Vittorio Org Lett [Image: see text] The sequential installation of a carbenoid and a hydride into a carbonyl, furnishing halomethyl alkyl derivatives, is reported. Despite the employment of carbenoids as nucleophiles in reactions with carbon-centered electrophiles, sp(3)-type alkyl halides remain elusive materials for selective one-carbon homologations. Our tactic levers on using carbonyls as starting materials and enables uniformly high yields and chemocontrol. The tactic is flexible and is not limited to carbenoids. Also, diverse carbanion-like species can act as nucleophiles, thus making it of general applicability. American Chemical Society 2020-09-10 2020-10-02 /pmc/articles/PMC8011987/ /pubmed/32910659 http://dx.doi.org/10.1021/acs.orglett.0c02831 Text en Permits the broadest form of re-use including for commercial purposes, provided that author attribution and integrity are maintained (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Miele, Margherita
Citarella, Andrea
Langer, Thierry
Urban, Ernst
Zehl, Martin
Holzer, Wolfgang
Ielo, Laura
Pace, Vittorio
Chemoselective Homologation–Deoxygenation Strategy Enabling the Direct Conversion of Carbonyls into (n+1)-Halomethyl-Alkanes
title Chemoselective Homologation–Deoxygenation Strategy Enabling the Direct Conversion of Carbonyls into (n+1)-Halomethyl-Alkanes
title_full Chemoselective Homologation–Deoxygenation Strategy Enabling the Direct Conversion of Carbonyls into (n+1)-Halomethyl-Alkanes
title_fullStr Chemoselective Homologation–Deoxygenation Strategy Enabling the Direct Conversion of Carbonyls into (n+1)-Halomethyl-Alkanes
title_full_unstemmed Chemoselective Homologation–Deoxygenation Strategy Enabling the Direct Conversion of Carbonyls into (n+1)-Halomethyl-Alkanes
title_short Chemoselective Homologation–Deoxygenation Strategy Enabling the Direct Conversion of Carbonyls into (n+1)-Halomethyl-Alkanes
title_sort chemoselective homologation–deoxygenation strategy enabling the direct conversion of carbonyls into (n+1)-halomethyl-alkanes
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8011987/
https://www.ncbi.nlm.nih.gov/pubmed/32910659
http://dx.doi.org/10.1021/acs.orglett.0c02831
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