A visible-light-induced, metal-free bis-arylation of 2,5-dichlorobenzoquinone

• Pieterjan Winant and
• Wim Dehaen

Beilstein J. Org. Chem. 2021, 17, 2315–2320, doi:10.3762/bjoc.17.149

• salts; Green Chemistry; Meerwein arylation; photoredox; Introduction Quinones or quinoid-based structures are ubiquitous in nature [1][2][3]. These versatile structures have shown promising antimalarial [4][5], antibacterial [6], and chemotherapeutic [6][7][8] properties. Their inherent oxidative

• , aryldiazonium salts have long played an essential role as radical precursors [20]. Their use in CH-arylation reactions of olefins, catalyzed by copper salts, was first published by Meerwein in 1939 [21]. Recently, we published a Meerwein arylation/cyclization sequence to benzofuropyridine derivatives in this

Photocatalysis with organic dyes: facile access to reactive intermediates for synthesis

• Stephanie G. E. Amos,
• Marion Garreau,
• Luca Buzzetti and
• Jerome Waser

Beilstein J. Org. Chem. 2020, 16, 1163–1187, doi:10.3762/bjoc.16.103

• important intermediates to develop new synthetic methods [62]. Their reactivity was first explored in the Meerwein arylation as well as the Gomberg–Bachman and the Sandmeyer reaction [63][64][65]. Similar to C(sp3) radicals, aryl radicals add to unsaturated systems, such as (hetero)arenes, alkenes, or

Recent advances in photocatalyzed reactions using well-defined copper(I) complexes

• Mingbing Zhong,
• Xavier Pannecoucke,
• Philippe Jubault and
• Thomas Poisson

Beilstein J. Org. Chem. 2020, 16, 451–481, doi:10.3762/bjoc.16.42

• excellent yields. Finally, a Meerwein arylation reaction was developed through the copper photocatalyzed formation of an aryl radical according to a reductive process. A large panel of aryl iodides was added to various pyrroles and electron-rich aromatic derivatives. The arylated products were obtained in

• aryl radical on ynamides or cyanamides, followed by a final cyclization. Using similar reaction conditions as those used for the Meerwein arylation, the three alkaloids were synthesized in good to excellent yield in a straightforward manner. In 2017, Fu, Peters, and co-workers reported the copper

• )(xantphos)]PF6. Chlorosulfonylation of styrene and alkyne derivatives by ATRA reactions. Reduction of aryl and alkyl halides with the complex [Cu(I)(bcp)(DPEPhos)]PF6. aIrradiation was carried out at 420 nm. All redox potential are reported vs SCE. Meerwein arylation of electron-rich aromatic derivatives

Polysubstituted ferrocenes as tunable redox mediators

• Sven D. Waniek,
• Jan Klett,
• Christoph Förster and
• Katja Heinze

Beilstein J. Org. Chem. 2018, 14, 1004–1015, doi:10.3762/bjoc.14.86

• syntheses [17][18][19][20][21][22][23][24][25][26][27][28]. Tuning of the electrochemical potential of substituted ferrocenium salts promoted a selective oxidative bicyclization reaction under mild conditions (Scheme 1a) [27]. Ferrocene and decamethylferrocene act as redox catalysts in Meerwein arylation

Photocatalyzed synthesis of isochromanones and isobenzofuranones under batch and flow conditions

• Manuel Anselmo,
• Lisa Moni,
• Hossny Ismail,
• Davide Comoretto,
• Renata Riva and
• Andrea Basso

Beilstein J. Org. Chem. 2017, 13, 1456–1462, doi:10.3762/bjoc.13.143

• ; photocatalysis; photo-Meerwein arylation–addition; Introduction Photoinduced multicomponent reactions are currently receiving remarkable attention [1]. Indeed, the possibility to obtain multiple-bond forming reactions under clean and mild conditions is nowadays one of the main targets of green chemistry

Pyridine-promoted dediazoniation of aryldiazonium tetrafluoroborates: Application to the synthesis of SF₅-substituted phenylboronic esters and iodobenzenes

• George Iakobson,
• Junyi Du,
• Alexandra M. Z. Slawin and
• Petr Beier

Beilstein J. Org. Chem. 2015, 11, 1494–1502, doi:10.3762/bjoc.11.162

• for an efficient reaction. Alkali metal acetates are known to facilitate decomposition of aryldiazonium salts by the formation of diazoacetates and diazo anhydrides, which decompose to aryl radicals [76]. These additives were used in Meerwein arylation of isopropenyl acetate [77]. In our case, two

An overview of the synthetic routes to the best selling drugs containing 6-membered heterocycles

• Marcus Baumann and
• Ian R. Baxendale

Beilstein J. Org. Chem. 2013, 9, 2265–2319, doi:10.3762/bjoc.9.265

• (Scheme 13). Removal of the acetyl protecting group under acidic conditions renders aniline 1.76 which is subsequently subjected to a Meerwein arylation reaction which occurs via diazotisation and subsequent treatment with acrylonitrile in the presence of cuprous oxide [45][46][47][48]. Alternatively, an