A review of recent advances in electrochemical and photoelectrochemical late-stage functionalization classified by anodic oxidation, cathodic reduction, and paired electrolysis

• Nian Li,
• Ruzal Sitdikov,
• Ajit Prabhakar Kale,
• Joost Steverlynck,
• Bo Li and
• Magnus Rueping

Beilstein J. Org. Chem. 2024, 20, 2500–2566, doi:10.3762/bjoc.20.214

Photoredox-catalyzed intramolecular nucleophilic amidation of alkenes with β-lactams

• Valentina Giraldi,
• Giandomenico Magagnano,
• Daria Giacomini,
• Pier Giorgio Cozzi and
• Andrea Gualandi

Beilstein J. Org. Chem. 2024, 20, 2461–2468, doi:10.3762/bjoc.20.210

• ; Introduction Access to nitrogen radicals for the functionalization of alkenes is a field under active investigation [1][2][3][4], as it gives the possibility to directly introduce nitrogen into an alkyl chain (alkene carboamination) to obtain valuable nitrogen-containing molecules [5][6]. Among several N

• alkenes due to their higher oxidation potential. Biological studies concerning the new derivatives will also be a subject of future investigations. A) Photoredox amidocyclization reaction. B) The strongly oxidizing Fukuzumi catalyst (I) used in the functionalization of alkenes by amides, and more recent

NaI/PPh₃-catalyzed visible-light-mediated decarboxylative radical cascade cyclization of N-arylacrylamides for the efficient synthesis of quaternary oxindoles

• Dan Liu,
• Yue Zhao and
• Frederic W. Patureau

Beilstein J. Org. Chem. 2023, 19, 57–65, doi:10.3762/bjoc.19.5

• future synthetic developments [61][62][63][64][65][66][67]. The NaI/PPh3 system has been further broadly applied to the functionalization of alkenes [68][69][70], as well as to decarboxylative C(sp3)–X bond formation [71], cyclization of 1,7-enynes [72][73] and other reactions [74][75][76][77]. Inspired

Recent advances in hypervalent iodine(III)-catalyzed functionalization of alkenes

• Xiang Li,
• Pinhong Chen and
• Guosheng Liu

Beilstein J. Org. Chem. 2018, 14, 1813–1825, doi:10.3762/bjoc.14.154

• ) reagents have been well-developed and widely utilized in functionalization of alkenes, however, generally either stoichiometric amounts of iodine(III) reagents are required or stoichiometric oxidants such as mCPBA are employed to in situ generate iodine(III) species. In this review, recent developments of

• hypervalent iodine(III)-catalyzed functionalization of alkenes and asymmetric reactions using a chiral iodoarene are summarized. Keywords: asymmetric catalysis; functionalization of alkenes; hypervalent iodine(III); Introduction Hypervalent iodine(III) reagents, also named as λ3-iodanes, have been widely

• , α-functionalization of carbonyl compounds, spirocyclizations, as well as functionalization of alkenes and alkynes [10][11][12][13][14][15][16][17]. In recent years, especially the functionalization of alkenes has attracted much attention [18][19][20] and in some cases, hypervalent iodine(III

Hypervalent organoiodine compounds: from reagents to valuable building blocks in synthesis

• Gwendal Grelier,
• Benjamin Darses and
• Philippe Dauban

Beilstein J. Org. Chem. 2018, 14, 1508–1528, doi:10.3762/bjoc.14.128

• disubstituted products 1 and 2 are obtained respectively from aliphatic ketones and methyl aryl ketones. The reaction conditions have then been extended to the functionalization of alkenes to afford 1,2-halo-oxygenated compounds 3 (Scheme 2b) [29]. This transformation has recently been used for the

Versatile deprotonated NHC: C,N-bridged dinuclear iridium and rhodium complexes

• Albert Poater

Beilstein J. Org. Chem. 2016, 12, 117–124, doi:10.3762/bjoc.12.13

• effective for any catalytic reaction, but some successful applications were achieved in the field of Ru-catalyzed metathesis of olefins [9][10][11][12], Ir-catalyzed hydrogenation [13][14], Pd-catalyzed C=C coupling reactions [15][16], Ir-catalyzed CO2 fixation [17][18], and/or functionalization of alkenes

New developments in gold-catalyzed manipulation of inactivated alkenes

• Michel Chiarucci and
• Marco Bandini

Beilstein J. Org. Chem. 2013, 9, 2586–2614, doi:10.3762/bjoc.9.294

• functionalization of alkenes rely on the use of “oxidative strategies” exploiting the [Au(I)/Au(III)] or [Au(I)Au(I)/Au(II)Au(II)] catalytic couples that can be accessed through the use of a suitable exogenous oxidant (Figure 2, path c) [9]. Last but not least, the potential role of Brønsted acid co-catalysis

Multistep flow synthesis of vinyl azides and their use in the copper-catalyzed Huisgen-type cycloaddition under inductive-heating conditions

• Lukas Kupracz,
• Jan Hartwig,
• Jens Wegner,
• Sascha Ceylan and
• Andreas Kirschning

Beilstein J. Org. Chem. 2011, 7, 1441–1448, doi:10.3762/bjoc.7.168

• vinyltriazoles is reported. The synthesis relies on a stable polymer-bound equivalent of iodine azide that serves to carry out 1,2-functionalization of alkenes in a telescope flow protocol. The intermediate 2-iodo azides are subjected to a DBU-mediated polymer-supported elimination step yielding vinyl azides in

• afforded the functionalized polymer 5, which could be used for 1,2-functionalization of alkenes with the same efficiency as described in Table 1. In addition the protonated form of PS–DBU 10 was regenerated to PS–DBU 8 by rinsing the reactor with a 1 M solution of DBU (Scheme 4). Copper-catalyzed Huisgen