Palladium-Catalyzed Formal (5 + 2) Annulation between ortho-Alkenylanilides and Allenes

Borja Cendón; Noelia Casanova; Cezar C. Comanescu; Rebeca García-Fandiño; Andrés Seoane; Moisés Gulías; José L. Mascareñas

doi:10.1021/acs.orglett.7b00467

Palladium-Catalyzed Formal (5 + 2) Annulation between ortho-Alkenylanilides and Allenes

Borja Cendón
, Noelia Casanova
, Cezar C. Comanescu
, Rebeca García-Fandiño
, Andrés Seoane
, Moisés Gulías^*
, José L. Mascareñas

^*Corresponding author for this work

Research output: Indexed journal article › Article › peer-review

58 Citations (Scopus)

Abstract

2-Alkenyltriflylanilides react with allenes upon treatment with catalytic amounts of Pd(OAc)₂ and Cu(II) to give highly valuable 2,3-dihydro-1H-benzo[b]azepines, in good yields, and with very high regio- and diastereoselectivities. Density functional theory (DFT) calculations suggest that the C-H activation of the alkenylanilide involves a classical concerted metalation-deprotonation (CMD) mechanism.

Original language	English
Pages (from-to)	1674-1677
Number of pages	4
Journal	Organic Letters
Volume	19
Issue number	7
DOIs	https://doi.org/10.1021/acs.orglett.7b00467
Publication status	Published - 7 Apr 2017
Externally published	Yes

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title = "Palladium-Catalyzed Formal (5 + 2) Annulation between ortho-Alkenylanilides and Allenes",

abstract = "2-Alkenyltriflylanilides react with allenes upon treatment with catalytic amounts of Pd(OAc)2 and Cu(II) to give highly valuable 2,3-dihydro-1H-benzo[b]azepines, in good yields, and with very high regio- and diastereoselectivities. Density functional theory (DFT) calculations suggest that the C-H activation of the alkenylanilide involves a classical concerted metalation-deprotonation (CMD) mechanism.",

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

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year = "2017",

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doi = "10.1021/acs.orglett.7b00467",

language = "English",

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T1 - Palladium-Catalyzed Formal (5 + 2) Annulation between ortho-Alkenylanilides and Allenes

AU - Cendón, Borja

AU - Casanova, Noelia

AU - Comanescu, Cezar C.

AU - García-Fandiño, Rebeca

AU - Seoane, Andrés

AU - Gulías, Moisés

AU - Mascareñas, José L.

PY - 2017/4/7

Y1 - 2017/4/7

N2 - 2-Alkenyltriflylanilides react with allenes upon treatment with catalytic amounts of Pd(OAc)2 and Cu(II) to give highly valuable 2,3-dihydro-1H-benzo[b]azepines, in good yields, and with very high regio- and diastereoselectivities. Density functional theory (DFT) calculations suggest that the C-H activation of the alkenylanilide involves a classical concerted metalation-deprotonation (CMD) mechanism.

AB - 2-Alkenyltriflylanilides react with allenes upon treatment with catalytic amounts of Pd(OAc)2 and Cu(II) to give highly valuable 2,3-dihydro-1H-benzo[b]azepines, in good yields, and with very high regio- and diastereoselectivities. Density functional theory (DFT) calculations suggest that the C-H activation of the alkenylanilide involves a classical concerted metalation-deprotonation (CMD) mechanism.

UR - https://www.scopus.com/pages/publications/85017172705

U2 - 10.1021/acs.orglett.7b00467

DO - 10.1021/acs.orglett.7b00467

M3 - Article

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AN - SCOPUS:85017172705

SN - 1523-7060

VL - 19

SP - 1674

EP - 1677

JO - Organic Letters

JF - Organic Letters

IS - 7

ER -

Palladium-Catalyzed Formal (5 + 2) Annulation between ortho-Alkenylanilides and Allenes

Abstract

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