Enones as Alkenyl Reagents via Ligand-Promoted C-C Bond Activation

doi:10.1021/acscatal.1c04010

	Enones as Alkenyl Reagents via Ligand-Promoted C-C Bond Activation
	Li, Hanyuan 1; Wang, Mei-Ling 1; Liu, Yu-Wen 2; Li, Ling-Jun 1; Xu, Hui 1; Dai, Hui-Xiong 1
刊名	ACS CATALYSIS
	2021-12-12
页码	82-88
关键词	C-C bond activation enone olefination Pd-catalyzed late-stage diversification
ISSN号	2155-5435
DOI	10.1021/acscatal.1c04010
通讯作者	Dai, Hui-Xiong(hxdai@simm.ac.cn)
英文摘要	Complementary to C-H bond activation, C-C bond activation has emerged over the past few years as an increasingly powerful tool to access and modify complex molecules. Ketones, owing to their versatility and availability, provide a significant platform for C-C bond activating reactions. Herein, we reported a beta-carbon elimination strategy for alkene(sp(2))-C(O) bonds to realize the olefination of unstrained enones via a vinyl palladium species, which delivers a series of conjugated polyene compounds. The protocol features broad substrate scope, functional group tolerance, and can be extended to dibenzylideneacetone (dba) substrates for olefination, alkynylation, arylation, and amination, which demonstrates the generality of the approach and affords two valuable products in one pot. Furthermore, the modification of natural products (beta-ionone and acetyl cedrene) and synthesis of natural products (piperine, lignarenone, novenone) highlight the potential utility of the reaction.
资助项目	Shanghai Institute of Materia Medica ; Chinese Academy of Sciences ; NSFC[21772211] ; NSFC[21920102003] ; Youth Innovation Promotion Association CAS[2014229] ; Youth Innovation Promotion Association CAS[2018293] ; Science and Technology Commission of Shanghai Municipality[17JC1405000] ; Science and Technology Commission of Shanghai Municipality[21ZR1475400] ; Science and Technology Commission of Shanghai Municipality[18431907100] ; Program of Shanghai Academic Research Leader[19XD1424600] ; National Science & Technology Major Project Key New Drug Creation and Manufacturing Program, China[2018ZX09711002-006]
WOS关键词	CARBON-CARBON BONDS ; HECK REACTION ; CATALYZED FUNCTIONALIZATION ; MECHANISTIC INSIGHTS ; ALARM PHEROMONES ; ARYL KETONES ; CLEAVAGE ; DECARBONYLATION ; CYCLIZATIONS ; EFFICIENT
WOS研究方向	Chemistry
语种	英语
出版者	AMER CHEMICAL SOC
WOS记录号	WOS:000731618900001
内容类型	期刊论文
源URL	[http://119.78.100.183/handle/2S10ELR8/299202]
专题	中国科学院上海药物研究所
通讯作者	Dai, Hui-Xiong
作者单位	1.Univ Chinese Acad Sci, Shanghai Inst Mat Med, Chinese Acad Sci Key Lab Receptor Res, Shanghai 201203, Peoples R China 2.Univ Sci & Technol China, NanoSci & Technol Inst, Suzhou 215123, Jiangsu, Peoples R China
推荐引用方式 GB/T 7714	Li, Hanyuan,Wang, Mei-Ling,Liu, Yu-Wen,et al. Enones as Alkenyl Reagents via Ligand-Promoted C-C Bond Activation[J]. ACS CATALYSIS,2021:82-88.
APA	Li, Hanyuan,Wang, Mei-Ling,Liu, Yu-Wen,Li, Ling-Jun,Xu, Hui,&Dai, Hui-Xiong.(2021).Enones as Alkenyl Reagents via Ligand-Promoted C-C Bond Activation.ACS CATALYSIS,82-88.
MLA	Li, Hanyuan,et al."Enones as Alkenyl Reagents via Ligand-Promoted C-C Bond Activation".ACS CATALYSIS (2021):82-88.