Late-stage C(sp²)–H and C(sp³)–H glycosylation of C-aryl/alkyl glycopeptides: mechanistic insights and fluorescence labeling

Abstract

<p>C–H glycosylations of complex amino acids and peptides were accomplished through the assistance of triazole peptide-isosteres. The palladium-catalyzed glycosylation provided access to complex <italic>C</italic>-glycosides and fluorescent-labeled glycoamino acids.</p>

Prussian Blue Cathode Materials for Sodium‐Ion Batteries and Other Ion Batteries

“…Most significantly, PBA lattice is structurally and dimensionally stable with almost zero lattice strain toward the insertion/extraction processes of gust ions due to its robust and large 3D channel framework. As demonstrated in recent years, a number of highly crystallized PBA lattices such as Na 2 NiFe(CN) 6 , Na 2 CuFe(CN) 6 , and Na 2 CoFe(CN) 6 can be very well cycled over 1000 cycles with >85% capacity retention even in aqueous electrolytes . This appealing cycling performance of the PB materials is sufficiently acceptable for commercial development of SIBs.…”

“…Particularly, due to their large ionic channels and interstices in the lattice, PBs are one of the few host materials that can accommodate larger alkali cations, such as Na + and K + ions, for facile and reversible insertion reactions. Benefiting from this structural feature, PB compounds have been intensively investigated as a new alternative and low‐cost Na‐insertion cathode during past five years . Since each molecular formula of PBs contains two redox centers M +2/+3 and Fe +2/+3 , suggesting that PBs can reach a two‐electron redox capacity, corresponding to a reversible 2 Na + storage per molecular unit.…”

Emerging Organometallic Methods for the Synthesis of C‐Branched (Hetero)aryl, Alkenyl, and Alkyl Glycosides: C−H Functionalization and Dual Photoredox Approaches

“… A possible mechanism for the Pd II ‐catalyzed synthesis of aryl‐C‐Δ 1, 2 glycosides (X=no atom), according to reports by Ye and Ackermann [48, 49] . Except for the oxidative addition (OA) step, this mechanism is also reasonable for the synthesis of C‐aryl pyranosides (X=no atom, CH 2 , or O) similar to Chen's [50] work (see below).…”

“…reported on the same type of transformation involving an N ‐triazolyldimethylmethyl ( N ‐TAM) DG ( 5 ; Scheme 3). [49] Milder reaction conditions (80 °C) were used to afford, without the need for an additional ligand, monoglycosylated derivatives 6 in excellent yields (78–95 %), except in the case of the furan adduct (54 %).…”

“… Pd II ‐catalyzed synthesis of aryl‐C‐Δ 1, 2 glycosides reported by Ackermann et al [49] . Bn: benzyl.…”