Tran Ryan Q, Dinh Long P, Jacoby Seth A, Harris Nekoda W, Swann William A, Williamson Savannah N, Semsey Rebecca Y, Yet Larry
Department of Chemistry, University of South Alabama Mobile AL 36688 USA
RSC Adv. 2021 Aug 23;11(45):28347-28351. doi: 10.1039/d1ra05417a. eCollection 2021 Aug 16.
3-Aryl-1-phosphinoimidazo[1,5-]pyridine ligands were synthesized from 2-aminomethylpyridine as the initial substrate two complementary routes. The first synthetic pathway underwent the coupling of 2-aminomethylpyridine with substituted benzoyl chlorides, followed by cyclization, iodination and palladium-catalyzed cross-coupling phosphination reactions sequence to give our phosphorus ligands. In the second route, 2-aminomethylpyridine was cyclized with aryl aldehydes, followed by the iodination and palladium-catalyzed cross-coupling phosphination reactions to yield our phosphorus ligands. The 3-aryl-1-phosphinoimidazo[1,5-]pyridine ligands were evaluated in palladium-catalyzed sterically-hindered biaryl and heterobiaryl Suzuki-Miyaura cross-coupling reactions.
以2-氨基甲基吡啶为起始底物，通过两条互补路线合成了3-芳基-1-膦基咪唑并[1,5 -]吡啶配体。第一条合成途径是将2-氨基甲基吡啶与取代苯甲酰氯进行偶联，随后进行环化、碘化和钯催化的交叉偶联膦化反应序列，以得到我们的磷配体。在第二条路线中，2-氨基甲基吡啶与芳醛进行环化反应，接着进行碘化和钯催化的交叉偶联膦化反应，以生成我们的磷配体。对3-芳基-1-膦基咪唑并[1,5 -]吡啶配体在钯催化的空间位阻联芳基和杂联芳基铃木-宫浦交叉偶联反应中进行了评估。
