A series of 2- and 3-pyridyl sulfonate and tosylate esters of primary and secondary alcohols were synthesized and evaluated in the bromination reaction with MgBr2·Et2O. The greater coordinating ability of… Click to show full abstract
A series of 2- and 3-pyridyl sulfonate and tosylate esters of primary and secondary alcohols were synthesized and evaluated in the bromination reaction with MgBr2·Et2O. The greater coordinating ability of the 2-pyridyl sulfonate esters accounted for its observed superior reactivity and selectivity. Reaction of neopentyl and phenyl 2-pyridyl sulfonates with a variety of aryl and heteroaryl Li reagents led to 2-substituted pyridines at temperatures as low as −78 °C via an SNAr process. Mechanistic considerations are discussed.
Journal Title: Canadian Journal of Chemistry
Year Published: 2021
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