Rhodium-Catalyzed Oxidative C−H Arylation of 2-Arylpyridine Derivatives via Decarbonylation of Aromatic Aldehydes

Shuai, Qi; Yang, Luo; Guo, Xiangyu; Baslé, Olivier; Li, Chao‐Jun

doi:10.1021/ja105396b

Cited by 148 publications

(51 citation statements)

References 31 publications

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“…An ejection of carbon monoxide and subsequent oxidation of 20 could afford the deformylative product 10 . Although the aldehyde group is removable under mild reaction conditions, the aldehyde group herein could act as an activating group to promote 2‐amination/cyclization . The violet dimer 21 would be formed via dimerization of the carbene intermediate 20 .…”

Section: Resultsmentioning

confidence: 99%

Synthesis of Phaitanthrin E and Tryptanthrin through Amination/Cyclization Cascade

Abe

Terasaki

2018

Helvetica Chimica Acta

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Phaitanthrin E was biomimetically synthesized from methyl indole‐3‐carboxylate and methyl anthranilate or anthranilic acid using the ester group as an activating group. The reaction proceeds through NCS‐mediated dearomatization/TFA‐catalyzed protonation of indolenine/C(2) amination/Et3N‐promoted aromatization and cyclization in one‐pot procedure. This method is capable of converting simple biomass materials to phaitanthrin E. The synthesis not only allows assessment of antiproliferative activity, but also affords experimental support for the hypothetical biosynthetic pathway of phaitanthrin E. The resulting phaitanthrin E derivatives were evaluated for in vitro antiproliferative activity against human colorectal cancer cells (DLD‐1). The biogenetic intermediate of phaitanthrin E showed higher antiproliferative activity than the natural product, phaitanthrin E. Furthermore, a concise synthesis of tryptanthrin is also accomplished from indole‐3‐carbaldehyde and methyl anthranilate using the aldehyde group as an activating group.

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Section: Resultsmentioning

confidence: 99%

Synthesis of Phaitanthrin E and Tryptanthrin through Amination/Cyclization Cascade

Abe

Terasaki

2018

Helvetica Chimica Acta

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“…No desired product was obtained in the model system when [Ru 3 CO 12 ] or [Rh(cod)Cl] (cod=1,5‐cyclooctadiene) was applied as the catalyst. Interestingly, arylation products, formed by decarbonylation of aldehydes, were produced by using [(CO) 2 Rh(acac)] as the catalyst 4c. Later on, 2,3‐diarylquinoxalines were also explored as substrates 5.…”

Section: Discussionmentioning

confidence: 99%

Acylation of (Hetero)Arenes through CH Activation with Aroyl Surrogates

2015

Chemistry A European J

133

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In this Minireview, the major achievements in the acylation of arenes and heteroarenes by C-H activation with aroyl groups are summarized and discussed. As the products are carbonyl-containing compounds that are typical products from carbonylation chemistry, the possible inspirations for these reactions are also discussed, as are mechanistic issues and possible problems for carbonylative diaryl ketone synthesis by C-H activation.

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“…2‐[2‐(4‐Fluorobenzene)]phenylpyridine (3 e) : Prepared according to the general procedure to afford 3 e as a white solid (57 mg, 72 % yield). R f =0.30 (EtOAc/hexanes=1:8); m.p.=102–105 °C; IR (KBr):

\overset{ν}{true}

=3006, 2924, 1900, 1728, 1583, 1456, 1423, 1217, 1092, 839, 750, 557 cm −1 ; 1 H NMR (400 MHz, CDCl 3 ): δ =8.62 (s, 1 H), 7.73–7.60 (m, 1 H), 7.50–7.35 (m, 4 H), 7.16–7.05 (m, 3 H), 6.97–6.81 ppm (m, 3 H); 13 C NMR (100 MHz, CDCl 3 ): δ =161.9 ( J C−F =224.0 Hz), 159.1, 149.5, 139.5, 137.3, 135.4, 131.2 ( J C−F =8.0 Hz), 130.5, 130.4, 128.6, 127.8, 125.3, 121.5, 115.1, 114.9 ppm; HRMS (ESI) m / z : calcd for C 17 H 13 FN: 250.1027 [ M +H] + ; found: 250.1026.…”

Section: Methodsmentioning

confidence: 99%

Palladium‐Catalyzed Direct Monoarylation of Aryl C−H Bonds with Iodoarenes

Guo

et al. 2017

ChemCatChem

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The transition‐metal‐catalyzed direct arylation of nonactivated aryl C−H bonds with iodoarenes has emerged as an important method for the construction of biaryls. Generally, the direct arylation reaction proceeds in the presence of stoichiometric Ag additives; moreover, the diarylation product is often unavoidable if there are two identical aromatic C−H bonds in the substrate. Herein we disclose an efficient Pd(OAc)2/trifluoroacetic acid/O2 catalytic system that promotes direct arylation reactions of a variety of aromatic C−H bonds with diverse iodoarenes under Ag‐free conditions. The coupling reaction possesses a complete monoarylation selectivity. This approach provides a straightforward, facile, and economical route to biaryls.

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Rhodium-Catalyzed Oxidative C−H Arylation of 2-Arylpyridine Derivatives via Decarbonylation of Aromatic Aldehydes

Abstract: A new concept for aryl-aryl coupling that involves oxidative decarbonylative coupling of aryl C-H bonds and readily available aldehydes has been developed, achieving the aryl-aryl union with complete control of reaction sites.

Cited by 148 publications

References 31 publications

Synthesis of Phaitanthrin E and Tryptanthrin through Amination/Cyclization Cascade

Synthesis of Phaitanthrin E and Tryptanthrin through Amination/Cyclization Cascade

Acylation of (Hetero)Arenes through CH Activation with Aroyl Surrogates

Palladium‐Catalyzed Direct Monoarylation of Aryl C−H Bonds with Iodoarenes

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