Ligand-Enabled γ-C(sp(3))-H Olefination of Amines: En Route to Pyrrolidines

Journal of the American Chemical Society
Heng JiangJin-Quan Yu

Abstract

Pd(II)-catalyzed olefination of γ-C(sp(3))-H bonds of triflyl (Tf) and 4-nitrobenzenesulfonyl (Ns) protected amines is achieved. Subsequent aza-Wacker oxidative cyclization or conjugate addition of the olefinated intermediates provides a variety of C-2 alkylated pyrrolidines. Three pyridine- and quinoline-based ligands are developed to match different classes of amine substrates, demonstrating a rare example of ligand-enabled C(sp(3))-H olefination reactions. The use of Ns protecting group to direct C(sp(3))-H activation of alkyl amines is also a significant step toward practical C-H functionalizations of alkyl amines.

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Citations

Aug 17, 2016·Journal of the American Chemical Society·Jing-Wen XuBing-Feng Shi
Sep 23, 2016·Journal of the American Chemical Society·Ke YangHaibo Ge
Oct 6, 2016·Organic Letters·Xiaolong YuJin Zhu
Nov 2, 2016·Journal of the American Chemical Society·Yongwei WuJin-Quan Yu
Dec 14, 2016·Journal of the American Chemical Society·Qiuping DingJin-Quan Yu
Feb 22, 2017·Chemical Communications : Chem Comm·Marta Pérez-GómezJosé-Antonio García-López
Jul 12, 2017·Dalton Transactions : an International Journal of Inorganic Chemistry·Yang-Yang XingDe-Zhan Chen
Mar 17, 2018·Dalton Transactions : an International Journal of Inorganic Chemistry·Jian-Biao LiuDe-Zhan Chen
Aug 19, 2016·Dalton Transactions : an International Journal of Inorganic Chemistry·Jia-Sheng OuyangFeng-Shou Liu
Nov 22, 2018·Angewandte Chemie·Padon ChuentragoolVladimir Gevorgyan
Sep 5, 2019·Angewandte Chemie·Daniel KaiserNuno Maulide
Apr 21, 2018·Chemical Science·Yan Xu, Guangbin Dong
Nov 7, 2017·Chemical Communications : Chem Comm·Neetipalli ThrimurtuluDebabrata Maiti
May 10, 2020·Angewandte Chemie·Han Seul ParkJin-Quan Yu
Mar 10, 2018·Beilstein Journal of Organic Chemistry·Mi-Hai LuoCheng-Chu Zeng
Jan 6, 2018·Organic & Biomolecular Chemistry·Pratik KumarScott T Laughlin
Jun 8, 2021·Chemical Science·Jayabrata DasDebabrata Maiti
Jun 25, 2021·Chemical Science·Wajid AliDebabrata Maiti
Dec 10, 2016·Organic Letters·Carolyn L Ladd, André B Charette
Sep 15, 2019·Journal of the American Chemical Society·Keita TanakaJin-Quan Yu
Apr 25, 2019·Organic Letters·Pratik KumarScott T Laughlin
Jan 30, 2018·The Journal of Organic Chemistry·Yong ZhengLijiang Xuan
Jul 22, 2018·Journal of the American Chemical Society·Zhe ZhuangJin-Quan Yu

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