Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, Singapore 637371, Singapore.
Graduate School of Pharmaceutical Sciences, Tohoku University, 6-3 Aoba, Aramaki, Aoba-ku, Sendai 980-8578, Japan.
Org Lett. 2022 Jan 14;24(1):430-434. doi: 10.1021/acs.orglett.1c04123. Epub 2021 Dec 28.
β-Iodo(III)enol carboxylates, phosphates, and tosylates can be efficiently synthesized through regio- and stereoselective iodo(III)functionalization of alkynes. The combination of chlorobenziodoxole and silver salt has proven to generate a versatile cationic iodine(III) electrophile to activate alkynes and engage various carboxylic acids, triethyl phosphate, and -toluenesulfonic acid as nucleophiles. The β-iodo(III)enol esters serve as starting materials for the synthesis of multisubstituted alkenes through sequential cross-coupling of the C-I(III) and C-O bonds.
β-碘(III)烯醇羧酸酯、磷酸酯和对甲苯磺酸盐可以通过炔烃的区域和立体选择性碘(III)官能化来高效合成。氯苯并二氧杂环戊烯和银盐的组合已被证明可以生成一种多功能的阳离子碘(III)亲电试剂，以激活炔烃并与各种羧酸、三乙磷酸酯和对甲苯磺酸作为亲核试剂反应。β-碘(III)烯醇酯可作为起始原料，通过 C-I(III)和 C-O 键的顺序交叉偶联来合成多取代烯烃。
