Carbohydrates, integral to numerous biological and pathogenic processes, are explored as pharmacophores despite their metabolic instability and high polarity, which compromise drug efficacy. Glycomimetics have emerged as a promising strategy to mimic the biological activities of carbohydrates while enhancing drug-like properties. For example, C2-allyl sugars, in which a C2-hydroxyl group is replaced by an allyl group, are useful synthons for glycomimics synthesis due to the versatile terminal olefins. Their application as intermediates was showcased in the synthesis of C2-ketonyl sugar derivatives (applications in metabolic polysaccharide remodeling and engineering), 13 rosaramicin (macrolide antibiotic), and an LpxC enzyme inhibitor (Figure ). Despite their high synthetic value, an efficient strategy to access C2-allyl sugars remains elusive. The superficially similar hydroxyl groups on the carbohydrate scaffold inevitably require prefunctionalization for regioselective control. To tackle site-selectivity challenges, a method involving the ring opening of epoxide sugars with allyl magnesium chloride produces C2-allyl sugars, while an alternative approach uses toxic tin allyl reagents for halogen substitution of C2-iodo sugars (Figure ). Thus, developing a catalytic process that simplifies access to C2-allylated sugars without employing toxic reagents is highly desirable.