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Where does Au coordinate to N-(2-pyridiyl)benzotriazole: gold-catalyzed chemoselective dehydrogenation and borrowing hydrogen reactions†
Organic Chemistry Frontiers ( IF 5.4 ) Pub Date : 2017-09-22 00:00:00 , DOI: 10.1039/c7qo00756f
Ronghui Huang 1, 2, 3, 4, 5 , Yongchun Yang 1, 2, 3, 4, 5 , Duo-Sheng Wang 6, 7, 8, 9 , Liang Zhang 4, 5, 10, 11 , Dawei Wang 1, 2, 3, 4, 5
Affiliation  

Where does Au coordinate to N-(2-pyridiyl)benzotriazole? Here, pyridyltriazole gold(I) complexes were synthesized, whereby it was revealed that the triazole part coordinated to gold(I). Compared to the Ph3PAuCl/AgOTf catalyst, pyridyltriazole gold(I) complexes proved to be an efficient pre-catalyst for the most challenging gold-catalyzed borrowing hydrogen reaction and dehydrogenation of alcohols and amines, which provided an efficient method to selectively synthesize imines, substituted amines and functionalized ketones in excellent yields with high chemoselectivity. This indicated that triazole ligands are helpful in forming gold nanoparticles and delaying agglomeration in these reactions. Importantly, this kind of air and moisture stable complex was effective for allene synthesis through the 3,3-rearrangement of propargyl ethers with good yields under wet conditions with a reduced catalyst loading by a silver-free protocol. Furthermore, the synthesis of 1,5-enyne derivatives was realized from propargyl alcohols with pyridyltriazole gold(I) complexes as the catalyst.

中文翻译:

Au与N-(2-吡啶基)苯并三唑配位的地方:金催化的化学选择性脱氢和借用的氢反应

Au在哪里与N-(2-吡啶基)苯并三唑配位?在此,合成了吡啶基三唑金(I)络合物,由此表明三唑部分与金(I)配位。与Ph 3 PAuCl / AgOTf催化剂相比,吡啶基三唑金(I)络合物被证明是最具挑战性的金催化借位氢反应以及醇和胺脱氢的有效预催化剂,这为选择性地合成亚胺,取代的胺和官能化的酮提供了一种有效的方法,该方法可以以高收率和高化学选择性选择性地合成亚胺,取代的胺和官能化的酮。这表明三唑配体有助于形成金纳米颗粒并延迟这些反应中的团聚。重要的是,这种空气和湿气稳定的络合物通过在湿润条件下以良好的收率进行炔丙基醚的3,3-重排,并通过无银方案降低了催化剂的负载量,对炔烃合成有效。此外,由炔丙基醇与吡啶基三唑金的合成实现了1,5-烯炔衍生物的合成(I)络合物作为催化剂。
更新日期:2017-09-22
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