We demonstrate that readily available and bench-stable α-oxo-vinylsulfones are competent electrophiles in Ni-catalyzed Suzuki–Miyaura cross-coupling reactions. The C–sulfone bond in the α-oxo-vinylsulfone motif is cleaved chemoselectively in these reactions, furnishing C-aryl glycals or acyclic vinyl ethers in high yields. These reactions proceed under mild conditions and tolerate a remarkable scope of heterocycles and functional groups. Preliminary mechanistic studies revealed the importance of an α-heteroatom in facilitating these transformations.

Ni-Catalyzed Suzuki-Miyaura Cross-Coupling of α-Oxo-vinylsulfones To Prepare C-Aryl Glycals and Acyclic Vinyl Ethers.

Regio- and diastereoselective Pd-catalyzed synthesis of C2-aryl glycosides

α,β‐Unsaturated 2‐Ketoglycosides via Pd‐Catalyzed Carbonylative Heck Reaction of 2‐Iodoglycals

Carbohydrate derivatives are fundamental and important class of bioactive compounds of life. For several decades, synthetic chemists have been directing their efforts to modify the carbohydrate/sugar molecules which have resulted in the development of innumerable methods to functionalize carbohydrate derivatives. In the last few years, the sp2 and sp3 C–H activation/functionalization of small organic molecules, using transition metal catalysts, such as those involving Pd-, Rh-, Cu-, Ni-, Ru-based catalysts, has emerged as important synthetic transformations in organic synthesis. The modification/functionalization of sp2 and sp3 C–H bonds of small organic molecules has been carried with or without the help of a directing group. The sp2 and sp3 C–H bond activation/functionalization methods have been well utilized to functionalize several types of small molecules comprising aliphatic, alicyclic aromatic, oxygen- and nitrogen-based heterocyclic compounds, and bioactive scaffolds such as amino acids, carbohydrates, and various natural products. In this chapter, we present the recent developments in the area pertaining to the synthesis of functionalized carbohydrate derivatives using transition metal–catalyzed C–H activation/functionalization strategy. Apart from the C–H activation/functionalization reactions, we have also presented some of the earlier approaches pertaining to the synthesis of functionalized carbohydrate derivatives involving the cross-coupling reaction and allylic/anomeric C–H functionalization of glycals. Furthermore, we have presented the developments in the synthesis of carbohydrate-based natural products, natural product derivatives, and pharmaceutical compounds involving the C–H activation/functionalization method.

Recent developments on the synthesis of functionalized carbohydrate/sugar derivatives involving the transition metal–catalyzed C–H activation/C–H functionalization

Herein, we reported the stereodivergent synthesis of C-glycosamino acids via Pd/Cu dual catalysis and found a suitable system to resolve many challenges, such as the tolerance towards the density of functional groups, the variability of the anomeric position, the compatibility of appropriate catalyst combinations, the regioselectivity of nucleophiles, and the match/mismatch problems between chiral substrates and chiral ligand-metal complexes. The method enables the efficient preparation of a series of unnatural C-glycosamino acid skeletons bearing two contiguous stereogenic centers in good yields with excellent diastereos-electivity. From this crucial precursor, various C-glycosamino acid derivatives have been achieved diversely. The readily prepared C-glycosamino acid hybrids will meet the growing demands for the development of new molecular entities for discovering new drugs and materials. This stereodivergent synthesis of C-glycosamino acids will further accelerate the study of their structural features, mode of action, and potential biological applications in the near future.

Stereodivergent synthesis of C -glycosamino acids via Pd/Cu dual catalysis

A stereospecific Mizoroki-Heck cross-coupling of differently substituted glycals with haloarenes resulting in the exclusive formation of either α- or β-aryl-C-glycosides depending solely on the configuration at C3 was achieved. The reaction was easy to set up because no specific precautions were required concerning moisture or oxygen, and it proceeded by a chirality transfer from C3 to C1. After optimization of cross-coupling conditions, various prepared glycals (7 examples) and arenes (10 examples) were tested, leading stereospecifically to the corresponding aryl-C-glycosides with a carbonyl group at C3, thus opening up new horizons for the total synthesis of glycosylated natural products.

/pdf/stereospecific-c-glycosylation-by-mizoroki-heck-reaction-a-2y5rfygmj1.pdf

Stereospecific C-Glycosylation by Mizoroki-Heck Reaction: A Powerful and Easy-to-Set-Up Synthetic Tool to Access α- and β-Aryl-C-Glycosides.

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Stereospecific C-Glycosylation by Mizoroki-Heck Reaction: A Powerful and Easy-to-Set-Up Synthetic Tool to Access α- and β-Aryl-C-Glycosides.