Direct preparation of benzylic manganese reagents from benzyl halides, sulfonates, and phosphates and their reactions: applications in organic synthesis

Mechanism and Applications of the Photoredox Catalytic Coupling of Benzyl Bromides

“…[1][2][3] The discoveryo ft he biological actions of dihydrostilbenoids, such as those of the combretastatin series, [4] have sparkedr enewed research interest in the synthesis of bibenzyl derivatives. The catalytic mechanism involves the oxidative addition of benzyl halides into low-valent complexes of Mn, [8,14,[25][26][27] Fe, [9,10,28] Ni, [20,22,29] Cu, [16-18, 30, 31] V, [32] Rh, [33] In, [34] Ti, [15,35] and Sm [36,37] that can be generated in the presence of electrons ourcesw ith very negative oxidationp otentials. To expand syntheticr outes to bibenzyls, novel methods that promote the Csp 3 -Csp 3 coupling of halomethyl arenes have been developed.…”

“…[5] However,t his method requires stoichiometric use of excessive reducing reagents, such as Li, [6,7] Mg, [8][9][10][11][12][13][14] Mn, [15,16] Fe, [17,18] Ni, [19] andZ n [20][21][22][23][24] metals, and this limits its syntheticu tility.T he recently developed methods of transition-metal-catalyzed Csp 3 -Csp 3 coupling enable increasedc ontrol over the reaction conditions. The catalytic mechanism involves the oxidative addition of benzyl halides into low-valent complexes of Mn, [8,14,[25][26][27] Fe, [9,10,28] Ni, [20,22,29] Cu, [16-18, 30, 31] V, [32] Rh, [33] In, [34] Ti, [15,35] and Sm [36,37] that can be generated in the presence of electrons ourcesw ith very negative oxidationp otentials. For instance, Zn metal is required to promotet he oxidative additiono fb enzylb romidesi nto aN i complex with at ridentate 2,6-bisoxazolylpyridine ligand.…”

Cobalt Catalysis Enables Regioselective Ring-opening of Epoxides with Aryl Halides

“…• NMR Spectroscopy: 1 H and 13 C NMR spectra were recorded at 25 °C on a Bruker 400 MHz, 500 MHz or Varian 600 MHz instrument with TMS as an internal standard. NMR chemical shifts are reported in ppm and referenced to the residual solvent peak of CDCl3 (7.26 ppm -1 H NMR and 77.16 ppm - 13 C NMR). Multiplicities are indicated by singlet (s), doublet (d), triplet (t), quartet (q), multiplet (m) and broad (br).…”

Synthesis of hydroxy benzoin/benzil analogs and investigation of their antioxidant, antimicrobial, enzyme inhibition, and cytotoxic activities

“…The benzoin condensation reaction is an important type of C-C bond formation reaction and is widely used to synthesize natural compounds and analogs. Symmetric and asymmetric benzoin derivative synthesis using different catalysts in benzoin condensation have been studied under milder reaction conditions [2][3][4][5][6][7][8][9][10][11][12][13][14][15]. However, the condensation of two different benzaldehydes may have a widely different character; only the more stable form of the isomeric mixed benzoins could be isolable in excess.…”

“…The significance of benzoin/benzil and carbohydrate-based agents caught our attention for the synthesis of benzoin/ benzil-O-β-D-glucosides, and we decided to study their pharmacological activities. Due to the biological activities' evaluation, we wish to report the synthesis of hydroxy benzoins (1-7) from hydroxy benzaldehydes, hydroxy benzils (8)(9)(10)(11)(12)(13)(14) from the oxidation of benzoins (1-7), and benzoin/benzil-O-β-D-glucosides (15)(16)(17)(18)(19)(20)(21)(22)(23)(24)(25) from the glycosylation of hydroxy benzoins/benzils (1)(2)(3)(4)(5)(6)(7)(8)(9)(10)(11)(12)(13)(14). Then, their antioxidant, antimicrobial, enzyme inhibitions, and cytotoxic activity investigations were reported.…”