Cauley Anthony N, Ramirez Antonio, Barhate Chandan L, Donnell Andrew F, Khandelwal Purnima, Sezen-Edmonds Melda, Sherwood Trevor C, Sloane Jack L, Cavallaro Cullen L, Simmons Eric M
Chemical Process Development, Bristol Myers Squibb, New Brunswick, New Jersey 08903, United States.
Small Molecule Drug Discovery, Bristol Myers Squibb, Princeton, New Jersey 08543, United States.
Org Lett. 2022 Aug 12;24(31):5663-5668. doi: 10.1021/acs.orglett.2c01942. Epub 2022 Aug 3.
Utilizing quinoline as a mild, catalytic additive, broadly applicable conditions for the Ni/photoredox-catalyzed C(sp)-C(sp) cross-coupling of (hetero)aryl bromides and alkyl pinacolboronate esters were developed, which can be applied to both batch and flow reactions. In addition to primary benzylic nucleophiles, both stabilized and nonstabilized secondary alkyl boronic esters are effective coupling partners. Density functional theory calculations suggest that alkyl radical generation occurs from an alkyl-B(pin)-quinoline complex, which may proceed via an energy transfer process.
利用喹啉作为温和的催化添加剂，开发了适用于（杂）芳基溴化物与烷基频哪醇硼酸酯的镍/光氧化还原催化C(sp)-C(sp)交叉偶联的广泛适用条件，该条件可应用于间歇反应和流动反应。除了伯苄基亲核试剂外，稳定和非稳定的仲烷基硼酸酯都是有效的偶联伙伴。密度泛函理论计算表明，烷基自由基的产生源于烷基-B(pin)-喹啉配合物，这可能通过能量转移过程进行。
