Redox-active molecules as organocatalysts for selective oxidative transformations – an unperceived organocatalysis field

• Elena R. Lopat’eva,
• Igor B. Krylov,
• Dmitry A. Lapshin and
• Alexander O. Terent’ev

Beilstein J. Org. Chem. 2022, 18, 1672–1695, doi:10.3762/bjoc.18.179

• aimed at overviewing the current state-of-art and perspectives of oxidative organocatalysis by redox-active molecules with the emphasis on challenging chemo-, regio- and stereoselective CH-functionalization processes. The catalytic systems based on N-oxyl radicals, amines, thiols, oxaziridines, ketone

• /peroxide, quinones, and iodine(I/III) compounds are the most developed catalyst types which are covered here. Keywords: CH-functionalization; free radicals; hypervalent iodine; N-oxyl radicals; redox-active molecules; Introduction Organocatalysis can be defined as catalysis by small organic molecules

• oxidative coupling processes (also known as cross-dehydrogenative coupling), as well as late-stage CH-functionalization. Oxidation processes are recognized as a challenge in fine organic synthesis technology [10][11] due to selectivity problems and frequent need for toxic transition metal salts and

On drug discovery against infectious diseases and academic medicinal chemistry contributions

• Yves L. Janin

Beilstein J. Org. Chem. 2022, 18, 1355–1378, doi:10.3762/bjoc.18.141

• example of a very late stage functionalization of molecule would be the use of zinc sulfinate chemistry [297] which, as depicted here, allowed to introduce in one step a trifluoromethyl group on the hydroquinidine 47 and access the otherwise rather hard-to-get compound 48. In fact, CH functionalization is

Hypervalent iodine compounds for anti-Markovnikov-type iodo-oxyimidation of vinylarenes

• Igor B. Krylov,
• Stanislav A. Paveliev,
• Mikhail A. Syroeshkin,
• Alexander A. Korlyukov,
• Pavel V. Dorovatovskii,
• Yan V. Zubavichus,
• Gennady I. Nikishin and
• Alexander O. Terent’ev

Beilstein J. Org. Chem. 2018, 14, 2146–2155, doi:10.3762/bjoc.14.188

• imide-N-oxyl radicals are used as effective mediators for CH-functionalization with formation of C–C, C–O, C–S, and C–N bonds [11][16][18][19][20][21][22][23][24][25][26][27][28][29][30][31][32][33][34][35][36][37][38][39][40][41][42]. Phthalimide-N-oxyl (PINO) is one of the most known imide-N-oxyl

Synthesis of dihydrophenanthridines by a sequence of Ugi-4CR and palladium- catalyzed intramolecular C-H functionalization

• Florence Bonnaterre,
• Michèle Bois-Choussy and
• Jieping Zhu

Beilstein J. Org. Chem. 2008, 4, No. 10, doi:10.3762/bjoc.4.10

• reaction pathway leading to the formation of oxindole via an intramolecular N-arylation process was not observed under these conditions [25][26][27]. The preferential formation of compound 1a indicated that cyclization via palladium-catalyzed CH functionalization could be, under appropriate conditions, a

• the Ugi adduct did not hamper the reaction, it actually accelerated the CH functionalization reaction. Furthermore, when two protons with similar steric environment were present, the more acidic one is activated selectively as it is observed in the cyclization of 6i (entry 9). In conclusion, we have