Yin, Lina ORCID: 0000-0002-6734-521X, Guan, Ting, Cheng, Jie, Pan, Dongchao, Lu, Jinyang, Huang, Jiahui, Wu, Jiaqi, Chen, Xiaoli, You, Taiyun, Huo, Xuting, He, Yuting, Pang, Jiayun ORCID: 0000-0003-0689-8440 and Hu, Qingzhong ORCID: 0000-0002-8880-4948 (2022) Manipulations of phenylnorbornyl palladium species for multicomponent construction of a bridged polycyclic privileged scaffold. Communications Chemistry, 5 (1):140. ISSN 2399-3669 (Online) (doi:https://doi.org/10.1038/s42004-022-00759-4)

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Abstract

Hexahydromethanocarbazole is a privileged scaffold in the discovery of new drugs and photoactive organic materials due to its good balance between structural complexity and minimized entropy penalty upon receptor binding. To address the difficulty of synthesizing this highly desirable bridged polycyclic scaffold, we designed a convenient multicomponent reaction cascade as intercepted Heck addition/C-H activation/C-palladacycle formation/electrophilic attack of ANP/N-palladacycle formation/Buchwald amination. A distinguishing feature of this sophisticated strategy is the successive generation of two key phenylnorbornyl palladium species to control the reaction flow towards desired products. DFT calculations further reveal the crucial roles of Cs2CO3 and 5,6-diester substitutions on the norbornene reactant in preventing multiple side-reactions. This innovative method exhibits a broad scope with good yields, and therefore will enable the construction of natural-product-like compound libraries based on hexahydromethanocarbazole.

Item Type:	Article
Uncontrolled Keywords:	hexahydromethanocarbazole; palladium; norbornene; privileged structure; DFT calculations; drug discovery
Subjects:	Q Science > QD Chemistry
Faculty / School / Research Centre / Research Group:	Faculty of Engineering & Science Faculty of Engineering & Science > School of Science (SCI)
Last Modified:	01 Nov 2022 16:20
URI:	http://gala.gre.ac.uk/id/eprint/37915

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