Direct Suzuki-Miyaura Coupling with Naphthalene-1,8-diaminato (dan)-Substituted Organoborons
Direct Suzuki-Miyaura Coupling with Naphthalene-1,8-diaminato (dan)-Substituted Organoborons
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1,8-萘-1,8-二氨基(dan)-取代的有机硼直接铃木-宫浦偶联
DOI：
10.1021/acscatal.9b03666
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发表时间：
2019
期刊：
影响因子：
12.9
通讯作者：
Tsuchimoto Teruhisa
中科院分区：
文献类型：
--
作者：
Yoshida Hiroto;Seki Michinari;Kamio Shintaro;Tanaka Hideya;Izumi Yuki;Li Jialun;Osaka Itaru;Abe Manabu;Andoh Hiroki;Yajima Tomoki;Tani Tomohiro;Tsuchimoto Teruhisa
事实证明，与“受保护的”R-B（dan）（dan =萘-1，8-二氨基）的实际直接Suzuki-Miyaura偶联可以顺利发生，而无需对B（dan）部分进行原位脱保护。在无水条件下使用t-BuOK（在某些情况下为Ba（OH）2）作为碱是成功交叉偶联的关键，其中R-B（dan）很容易转化为具有金属交换活性的硼酸盐形式，而不管公认的降低的硼-路易斯酸。
The actually direct Suzuki–Miyaura coupling with “protected” R–B(dan) (dan = naphthalene-1,8-diaminato) was demonstrated to smoothly occur without in situ deprotection of the B(dan) moiety. The use oft-BuOK (Ba(OH)2in some cases) as a base under anhydrous conditions is the key to the successful cross-coupling, where R–B(dan) is readily converted into a transmetalation-active borate-form, regardless of the well-accepted diminished boron-Lewis acidity.