Synthesis of Homoallylamines Enabled by Cobalt or Palladium Catalyzed Allylic Substitution of Azaarylmethylamines

Pd­(OAc)2/Nixantphos or CoI2/Nixantphos catalyzed allylic substitutions with weakly acidic C­(sp)3–H bonds of azaarylmethylamines are described. This method facilitates access to various kinds of heteroaryl rings containing homoallylamines (39 examples, 30–98% yields) with excellent functional group...

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Bibliographic Details
Published in:Organic letters 2024-04, Vol.26 (15), p.2982-2986
Main Authors: Zheng, Jiali, Hua, Rui, Wang, Yan-En, Lin, Tingzhi, Ou, Mingjie, Wu, Yu, Shi, En-hao, He, Jing, Xiong, Dan, Mao, Jianyou
Format: Article
Language:English
Subjects:
catalytic activity
cobalt
diastereoselectivity
enantioselectivity
heterocyclic compounds
palladium
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Summary:Pd­(OAc)2/Nixantphos or CoI2/Nixantphos catalyzed allylic substitutions with weakly acidic C­(sp)3–H bonds of azaarylmethylamines are described. This method facilitates access to various kinds of heteroaryl rings containing homoallylamines (39 examples, 30–98% yields) with excellent functional group tolerance and diastereoselectivity. Compared with the Pd/Nixantphos complex, the Co/Nixantphos catalysis could obtain the cyclic products with good to excellent diastereoselectivities. Importantly, the CoI2/(R,R)-Me-Duphos catalyzed reactions exhibit moderate enantioselectivity. Additionally, the scalability of this transformation is successfully demonstrated.
ISSN:1523-7060
1523-7052
1523-7052
DOI:10.1021/acs.orglett.4c00551