Rhodium(III)-Catalyzed Annulation of 2-Alkenyl Anilides with Alkynes through C−H Activation: Direct Access to 2-Substituted Indolines

Marc Font; Borja Cendón; Andrés Seoane; José Luis Mascareñas; Moisés Gulías

doi:10.1002/anie.201802830

Rhodium(III)-Catalyzed Annulation of 2-Alkenyl Anilides with Alkynes through C−H Activation: Direct Access to 2-Substituted Indolines

Marc Font, Borja Cendón, Andrés Seoane, José Luis Mascareñas^*, Moisés Gulías

^*Autor corresponent d’aquest treball

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A Rh^III complex featuring an electron-deficient η⁵-cyclopentadienyl ligand catalyzed an unusual annulation between alkynes and 2-alkenyl anilides to form synthetically appealing 2-substituted indolines. Formally, the process can be viewed as an allylic amination with concomitant hydrocarbonation of the alkyne. Mechanistic experiments indicate that this transformation involves an unusual rhodium migration with a concomitant 1,5-H shift.

Idioma original	Anglès
Pàgines (de-a)	8255-8259
Nombre de pàgines	5
Revista	Angewandte Chemie - International Edition
Volum	57
Número	27
DOIs	https://doi.org/10.1002/anie.201802830
Estat de la publicació	Publicada - 2 de jul. 2018
Publicat externament	Sí

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title = "Rhodium(III)-Catalyzed Annulation of 2-Alkenyl Anilides with Alkynes through C−H Activation: Direct Access to 2-Substituted Indolines",

abstract = "A RhIII complex featuring an electron-deficient η5-cyclopentadienyl ligand catalyzed an unusual annulation between alkynes and 2-alkenyl anilides to form synthetically appealing 2-substituted indolines. Formally, the process can be viewed as an allylic amination with concomitant hydrocarbonation of the alkyne. Mechanistic experiments indicate that this transformation involves an unusual rhodium migration with a concomitant 1,5-H shift.",

keywords = "annulation, C−H activation, indolines, rhodium, rhodium shift",

author = "Marc Font and Borja Cend{\'o}n and Andr{\'e}s Seoane and Mascare{\~n}as, \{Jos{\'e} Luis\} and Mois{\'e}s Gul{\'i}as",

note = "Publisher Copyright: {\textcopyright} 2018 Wiley-VCH Verlag GmbH \& Co. KGaA, Weinheim",

year = "2018",

month = jul,

day = "2",

doi = "10.1002/anie.201802830",

language = "English",

volume = "57",

pages = "8255--8259",

journal = "Angewandte Chemie - International Edition",

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Rhodium(III)-Catalyzed Annulation of 2-Alkenyl Anilides with Alkynes through C−H Activation: Direct Access to 2-Substituted Indolines. / Font, Marc; Cendón, Borja; Seoane, Andrés et al.
In: Angewandte Chemie - International Edition, Vol. 57, Núm. 27, 02.07.2018, pàg. 8255-8259.

Producció científica: Article en revista indexada › Article › Avaluat per experts

TY - JOUR

T1 - Rhodium(III)-Catalyzed Annulation of 2-Alkenyl Anilides with Alkynes through C−H Activation

T2 - Direct Access to 2-Substituted Indolines

AU - Font, Marc

AU - Cendón, Borja

AU - Seoane, Andrés

AU - Mascareñas, José Luis

AU - Gulías, Moisés

PY - 2018/7/2

Y1 - 2018/7/2

N2 - A RhIII complex featuring an electron-deficient η5-cyclopentadienyl ligand catalyzed an unusual annulation between alkynes and 2-alkenyl anilides to form synthetically appealing 2-substituted indolines. Formally, the process can be viewed as an allylic amination with concomitant hydrocarbonation of the alkyne. Mechanistic experiments indicate that this transformation involves an unusual rhodium migration with a concomitant 1,5-H shift.

AB - A RhIII complex featuring an electron-deficient η5-cyclopentadienyl ligand catalyzed an unusual annulation between alkynes and 2-alkenyl anilides to form synthetically appealing 2-substituted indolines. Formally, the process can be viewed as an allylic amination with concomitant hydrocarbonation of the alkyne. Mechanistic experiments indicate that this transformation involves an unusual rhodium migration with a concomitant 1,5-H shift.

KW - annulation

KW - C−H activation

KW - indolines

KW - rhodium

KW - rhodium shift

UR - https://www.scopus.com/pages/publications/85049001029

U2 - 10.1002/anie.201802830

DO - 10.1002/anie.201802830

M3 - Article

C2 - 29726603

AN - SCOPUS:85049001029

SN - 1433-7851

VL - 57

SP - 8255

EP - 8259

JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

IS - 27

ER -

Rhodium(III)-Catalyzed Annulation of 2-Alkenyl Anilides with Alkynes through C−H Activation: Direct Access to 2-Substituted Indolines

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