Chiral Pincer Carbodicarbene Ligands for Enantioselective Rhodium-Catalyzed Hydroarylation of Terminal and Internal 1,3-Dienes with Indoles

Chiral Pincer Carbodicarbene Ligands for Enantioselective Rhodium-Catalyzed Hydroarylation of Terminal and Internal 1,3-Dienes with Indoles
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DOI:
10.1021/jacs.7b08575
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发表时间:
2017-11-08
影响因子:
15
通讯作者:
Meek, Simon J.
Meek, Simon J.
中科院分区:
化学1区
文献类型:
--
作者:
Marcum, Justin S.;Roberts, Courtney C.;Meek, Simon J.

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报道了N-杂芳烃与末端和内部1,3-二烯的催化不对称加成反应。反应由5mol%的Rh催化剂和一种新的手性钳形碳二卡宾配体支撑,该配体能够以高达95%的产率和高达98:2Er的产率产生烯丙基取代芳烃。机理和X-射线证据支持反应通过Rh(III)-ETA(3-)烯丙基进行。
Catalytic enantioselective addition of N-heteroarenes to terminal and internal 1,3-dienes is reported. Reactions are promoted by 5 mol % of Rh catalyst supported by a new chiral pincer carbodicarbene ligand that delivers allylic substituted arenes in up to 95% yield and up to 98:2 er. Mechanistic and X-ray evidence is presented that supports that the reaction proceeds via a Rh(III)-eta(3-)allyl.