Double and Single Hydroboration of Nitriles Catalyzed by a Ruthenium-Bis(silyl)xanthene Complex: Application to One-Pot Synthesis of Diarylamines and N-Arylimines
Double and Single Hydroboration of Nitriles Catalyzed by a Ruthenium-Bis(silyl)xanthene Complex: Application to One-Pot Synthesis of Diarylamines and N-Arylimines
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DOI：
10.1021/acs.organomet.9b00064
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发表时间：
2019-04-08
期刊：
影响因子：
2.8
通讯作者：
Tobita, Hiromi
中科院分区：
文献类型：
--
作者：
Kitano, Takeo;Komuro, Takashi;Tobita, Hiromi
一种含双(硅基)黄杂菲螯合配体xantsil的Ru[kappa(3)(Si，O，Si)-xantsil](CO)(PCyp(3))(1a，Cyp=环戊基)催化了双和单氢化反应，分别得到双(硼基)胺2和N-硼亚胺3。通过将这些反应与钯催化的2和3与溴代芳烃和(Kobu)-Bu-t的1：1混合物的脱氧C-N偶联反应相结合，开发了由腈合成N，N-二芳胺4和N-芳醛二胺5的一锅法路线。
A ruthenium complex bearing a bis(silyl)xanthene chelate ligand xantsil, i.e. Ru[kappa(3)(Si, O, Si)-xantsil](CO)(PCyp(3)) (1a, Cyp = cyclopentyl), was found to catalyze both double and single hydroboration reactions of nitriles with pinacolborane (HBpin) and 9-borabicyclo[3.3.1]nonane (9-BBN) to give bis(boryl)amines 2 and N-borylimines 3, respectively, in mostly >99% yields. By combination of these reactions with subsequent palladium-catalyzed deborylative C-N coupling reactions of 2 and 3 with a 1:1 mixture of bromoarenes and (KOBu)-Bu-t, one-pot synthetic routes to tertiary N,N-diarylamines 4 and N-arylaldimines 5 from nitriles were developed.