Metal-Free, Brønsted Acid-Catalyzed Formal [3+2] Annulation of Quinone Monoacetals with 2-Naphthols

Anu Jacob; Tony Roy; Trinadh Kaicharla; Akkattu T. Biju

doi:10.1021/acs.joc.7b02033

Metal-Free, Brønsted Acid-Catalyzed Formal [3+2] Annulation of Quinone Monoacetals with 2-Naphthols

Anu Jacob, Tony Roy, Trinadh Kaicharla, Akkattu T. Biju

Research output: Contribution to journal › Article › peer-review

26 Scopus citations

Abstract

An operationally simple and metal-free cross-coupling of quinone monoacetals (QMAs) with 2-naphthols catalyzed by triflic acid is reported. This formal [3+2] annulation allowed the synthesis of diverse naphtho[2,1-b]benzofuran derivatives in moderate to good yields. Preliminary mechanistic studies reveal the initial nucleophilic substitution of QMAs with 2-naphthols in preference to the mixed acetal formation and subsequent [3,3] sigmatropic rearrangement.

Original language	English (US)
Pages (from-to)	11269-11274
Number of pages	6
Journal	Journal of Organic Chemistry
Volume	82
Issue number	20
DOIs	https://doi.org/10.1021/acs.joc.7b02033
State	Published - Oct 20 2017
Externally published	Yes

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© 2017 American Chemical Society.

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abstract = "An operationally simple and metal-free cross-coupling of quinone monoacetals (QMAs) with 2-naphthols catalyzed by triflic acid is reported. This formal [3+2] annulation allowed the synthesis of diverse naphtho[2,1-b]benzofuran derivatives in moderate to good yields. Preliminary mechanistic studies reveal the initial nucleophilic substitution of QMAs with 2-naphthols in preference to the mixed acetal formation and subsequent [3,3] sigmatropic rearrangement.",

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AU - Jacob, Anu

AU - Roy, Tony

AU - Kaicharla, Trinadh

AU - Biju, Akkattu T.

PY - 2017/10/20

Y1 - 2017/10/20

N2 - An operationally simple and metal-free cross-coupling of quinone monoacetals (QMAs) with 2-naphthols catalyzed by triflic acid is reported. This formal [3+2] annulation allowed the synthesis of diverse naphtho[2,1-b]benzofuran derivatives in moderate to good yields. Preliminary mechanistic studies reveal the initial nucleophilic substitution of QMAs with 2-naphthols in preference to the mixed acetal formation and subsequent [3,3] sigmatropic rearrangement.

AB - An operationally simple and metal-free cross-coupling of quinone monoacetals (QMAs) with 2-naphthols catalyzed by triflic acid is reported. This formal [3+2] annulation allowed the synthesis of diverse naphtho[2,1-b]benzofuran derivatives in moderate to good yields. Preliminary mechanistic studies reveal the initial nucleophilic substitution of QMAs with 2-naphthols in preference to the mixed acetal formation and subsequent [3,3] sigmatropic rearrangement.

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Metal-Free, Brønsted Acid-Catalyzed Formal [3+2] Annulation of Quinone Monoacetals with 2-Naphthols

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