Preparation of Benzolactams by Pd(OAc)<sub>2</sub>-Catalyzed Direct Aromatic Carbonylation

Orito, Kazuhiko; Horibata, Akiyoshi; Nakamura, Takatoshi; Ushito, Harumi; Nagasaki, Hideo; Yuguchi, Motoki; Yamashita, Satoshi; Tokuda, Masao

doi:10.1021/ja045342+

Cited by 298 publications

(120 citation statements)

References 4 publications

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“…Orito and co-workers prepared a variety of five-or six-membered benzolactams by the direct aromatic carbonylation of secondary ω-phenylalkylamines using Pd(OAc) 2 and Cu(OAc) 2 in an atmosphere of CO gas containing air (Scheme 33) [99,100]. In 2007, they applied this methodology to the synthesis of N-protected staurosporinones [101].…”

Section: Synthesis Of Five-membered Heterocycles Via Oxidative Carbonmentioning

confidence: 99%

Synthesis of Functionalized Heterocycles via Oxidative Carbonylation

Xing

2015

Topics in Heterocyclic Chemistry

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With the assistance of a proper oxidant, carbonylation of two nucleophiles can take place directly in carbonylation conditions, which is defined as oxidative carbonylation. This process starts with the reaction of nucleophiles with the metal catalyst in oxidation state (M (n + 2) ), followed by insertion of CO and subsequent reductive elimination, providing the carbonylated products and the metal catalyst in reduction state (M (n) ). The oxidant could reoxidize M (n) to M (n + 2) to promote the catalytic cycle. Oxidative carbonylation avoids the difficult oxidative addition of R-X to metal catalyst, so this kind of carbonylation could proceed in mild conditions. What's more is that oxidative carbonylation doesn't need prefunctionalization of substrates. So, it's no wonder that considerable attention has been drawn to construct important carbonylated compounds through oxidative carbonylation. Particularly, much progress in synthesis of carbonylated heterocycles via oxidative carbonylation has been achieved in the past decades. Here, we summarized the main achievements in this area from 1982 to the beginning of 2015.

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Section: Synthesis Of Five-membered Heterocycles Via Oxidative Carbonmentioning

confidence: 99%

Synthesis of Functionalized Heterocycles via Oxidative Carbonylation

Xing

2015

Topics in Heterocyclic Chemistry

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“…B. N-Alkylbenzylaminen oder N-Alkylphenethylaminen, zur Bildung verschiedener fünf-oder sechsgliedriger Benzolactame (Schema 24). [97] In einem CO/Luft-Gemisch wurden katalytische Mengen Pd(OAc) 2 und Cu(OAc) 2 eingesetzt. Es wurde angenommen, dass die Carbonylierung unter ortho-Palladierung abläuft, was zu einer bemerkenswerten Regioselektivität führte.…”

Section: Im Jahr 2004 Beschrieben Orito Et Al Die Pdunclassified

Oxidative Carbonylierungen: Organometallverbindungen (RM) oder Kohlenwasserstoffe (RH) als Nucleophile

2011

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Oxidative Carbonylierungen haben in den letzten Jahren ein breites Interesse geweckt, und insbesondere die Synthese von Carbonat‐ und Harnstoffderivaten durch oxidative Carbonylierung von Alkoholen und Aminen wurde intensiv untersucht. Eine neuartige Entwicklung ist die direkte Verwendung von Organometallverbindungen (RM) und Kohlenwasserstoffen (RH) als Nucleophile zum Aufbau einer C‐C‐Bindung in oxidativen Carbonylierungen. Dieser Kurzaufsatz stellt diese neue Art der oxidativen Carbonylierung vor.

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“…Tetraacetyl riboflavin, 10 N-propyl-4-methoxybenzylamine (3e), 15 2-(4-methoxyphenyl)ethanamine (3k), 16 Bzl-Phe-OMe (9), MobPhe-OMe (11), Mob-Ala-OMe (12), 17 Mob-Pro-OMe (14), 18 BzlPro-OMe (16), 19 Boc-Phe-OMob (21), 20 Boc-Phe-OBzl (23), 21 tertbutyl 1-(benzyloxy)-3-phenylpropan-2-ylcarbamate (27), 22 and Cbz-(OH)-Pro-OBzl (31), 23 were prepared as previously reported. All other chemicals were purchased from commercial suppliers and used as received.…”

Section: Photocatalytic Cleavage Of Benzyl Protecting Groupsmentioning

confidence: 99%

Oxidation and Deprotection of Primary Benzylamines by Visible Light Flavin Photocatalysis

Lechner¹,

König²

2010

Synthesis

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We report a photocatalytic oxidation procedure that can be used to convert benzylamines into their corresponding aldehydes under mild conditions without over-oxidation, using riboflavin tetraacetate as photocatalyst and blue emitting LEDs (440 nm) as light source. Oxygen is the terminal oxidant and H 2 O 2 and NH 3 appear as the only byproducts of the oxidation of primary benzylamines. Furthermore, we have developed a photocatalytic protocol for 4-methoxybenzyl (Mob) group deprotection of primary amines and alcohols. Double bonds, benzyl-protected esters and alcohols are tolerated under the applied conditions, whereas the deprotection of protected secondary amines is not applicable. Mob-protected carboxylic acids and carboxybenzoyl (Cbz) protected amines are inert under the photodeprotection conditions.

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Preparation of Benzolactams by Pd(OAc)₂-Catalyzed Direct Aromatic Carbonylation

Cited by 298 publications

References 4 publications

Synthesis of Functionalized Heterocycles via Oxidative Carbonylation

Synthesis of Functionalized Heterocycles via Oxidative Carbonylation

Oxidative Carbonylierungen: Organometallverbindungen (RM) oder Kohlenwasserstoffe (RH) als Nucleophile

Oxidation and Deprotection of Primary Benzylamines by Visible Light Flavin Photocatalysis

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Preparation of Benzolactams by Pd(OAc)2-Catalyzed Direct Aromatic Carbonylation

Cited by 298 publications

References 4 publications

Synthesis of Functionalized Heterocycles via Oxidative Carbonylation

Synthesis of Functionalized Heterocycles via Oxidative Carbonylation

Oxidative Carbonylierungen: Organometallverbindungen (RM) oder Kohlenwasserstoffe (RH) als Nucleophile

Oxidation and Deprotection of Primary Benzylamines by Visible Light Flavin Photocatalysis

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Preparation of Benzolactams by Pd(OAc)₂-Catalyzed Direct Aromatic Carbonylation