Rhodium-Catalyzed Annulation of ortho-Alkenyl Anilides with Alkynes: Formation of Unexpected Naphthalene Adducts

Andrés Seoane; Cezar Comanescu; Noelia Casanova; Rebeca García-Fandiño; Xabier Diz; José L. Mascareñas; Moisés Gulías

doi:10.1002/anie.201811747

Rhodium-Catalyzed Annulation of ortho-Alkenyl Anilides with Alkynes: Formation of Unexpected Naphthalene Adducts

Andrés Seoane, Cezar Comanescu, Noelia Casanova, Rebeca García-Fandiño, Xabier Diz, José L. Mascareñas, Moisés Gulías

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

33 Cites (Scopus)

Resum

o-Alkenyl N-triflylanilides underwent rhodium(III)-catalyzed oxidative annulations with alkynes to produce different types of naphthylamides in a process which involves the cleavage of two C−H bonds. Remarkably, besides formal dehydrogenative (4C+2C) cycloadducts, the reaction also produces variable amounts of isomeric naphthylamides, whose formation requires a formal migration of the alkenyl moiety from the ortho to the meta position of the anilide. The annulation reaction can be efficiently carried out in the absence of external oxidants, such as Cu(OAc) ₂ .

Idioma original	Anglès
Pàgines (de-a)	1700-1704
Nombre de pàgines	5
Revista	Angewandte Chemie - International Edition
Volum	58
Número	6
DOIs	https://doi.org/10.1002/anie.201811747
Estat de la publicació	Publicada - 4 de febr. 2019
Publicat externament	Sí

Accés al document

10.1002/anie.201811747

Altres arxius i enllaços

Enllaç a la publicació de Scopus

Com citar-ho

@article{fa76afa1c6c24cb3814afe0cef073abb,

title = "Rhodium-Catalyzed Annulation of ortho-Alkenyl Anilides with Alkynes: Formation of Unexpected Naphthalene Adducts",

abstract = " o-Alkenyl N-triflylanilides underwent rhodium(III)-catalyzed oxidative annulations with alkynes to produce different types of naphthylamides in a process which involves the cleavage of two C−H bonds. Remarkably, besides formal dehydrogenative (4C+2C) cycloadducts, the reaction also produces variable amounts of isomeric naphthylamides, whose formation requires a formal migration of the alkenyl moiety from the ortho to the meta position of the anilide. The annulation reaction can be efficiently carried out in the absence of external oxidants, such as Cu(OAc) 2 .",

keywords = "anilides, annulation, C−H activation, naphthylamines, rhodium",

author = "Andr{\'e}s Seoane and Cezar Comanescu and Noelia Casanova and Rebeca Garc{\'i}a-Fandi{\~n}o and Xabier Diz and Mascare{\~n}as, {Jos{\'e} L.} and Mois{\'e}s Gul{\'i}as",

note = "Publisher Copyright: {\textcopyright} 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim",

year = "2019",

month = feb,

day = "4",

doi = "10.1002/anie.201811747",

language = "English",

volume = "58",

pages = "1700--1704",

journal = "Angewandte Chemie - International Edition",

issn = "1433-7851",

publisher = "John Wiley and Sons Ltd",

number = "6",

}

TY - JOUR

T1 - Rhodium-Catalyzed Annulation of ortho-Alkenyl Anilides with Alkynes

T2 - Formation of Unexpected Naphthalene Adducts

AU - Seoane, Andrés

AU - Comanescu, Cezar

AU - Casanova, Noelia

AU - García-Fandiño, Rebeca

AU - Diz, Xabier

AU - Mascareñas, José L.

AU - Gulías, Moisés

PY - 2019/2/4

Y1 - 2019/2/4

N2 - o-Alkenyl N-triflylanilides underwent rhodium(III)-catalyzed oxidative annulations with alkynes to produce different types of naphthylamides in a process which involves the cleavage of two C−H bonds. Remarkably, besides formal dehydrogenative (4C+2C) cycloadducts, the reaction also produces variable amounts of isomeric naphthylamides, whose formation requires a formal migration of the alkenyl moiety from the ortho to the meta position of the anilide. The annulation reaction can be efficiently carried out in the absence of external oxidants, such as Cu(OAc) 2 .

AB - o-Alkenyl N-triflylanilides underwent rhodium(III)-catalyzed oxidative annulations with alkynes to produce different types of naphthylamides in a process which involves the cleavage of two C−H bonds. Remarkably, besides formal dehydrogenative (4C+2C) cycloadducts, the reaction also produces variable amounts of isomeric naphthylamides, whose formation requires a formal migration of the alkenyl moiety from the ortho to the meta position of the anilide. The annulation reaction can be efficiently carried out in the absence of external oxidants, such as Cu(OAc) 2 .

KW - anilides

KW - annulation

KW - C−H activation

KW - naphthylamines

KW - rhodium

UR - http://www.scopus.com/inward/record.url?scp=85059835817&partnerID=8YFLogxK

U2 - 10.1002/anie.201811747

DO - 10.1002/anie.201811747

M3 - Article

C2 - 30507055

AN - SCOPUS:85059835817

SN - 1433-7851

VL - 58

SP - 1700

EP - 1704

JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

IS - 6

ER -

Rhodium-Catalyzed Annulation of ortho-Alkenyl Anilides with Alkynes: Formation of Unexpected Naphthalene Adducts

Resum

Accés al document

Altres arxius i enllaços

Fingerprint

Com citar-ho