A Simple Aliphatic Diamine Auxiliary for Palladium‐Catalyzed Arylation of Unactivated β‐C(sp3)‐H Bonds. Issue 23 (16th October 2018)

• Record Type: Journal Article
• Authors: Lou, Jiang; Wang, Quannan; He, Yuan; Yu, Zhengkun
• Is Part Of: Advanced synthesis & catalysis. Volume 360:Issue 23(2018)
• Page Start: 4571
• Page End: 4584
• Publication Date: 2018-10-16
• Subjects: diamine -- directing groups -- palladium -- C−H activation -- hydrocinnamic acids; Catalysis -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Chemistry -- Periodicals; Chemistry, Technical -- Periodicals; Chemistry -- Periodicals; Catalysis -- Periodicals; Technology, Pharmaceutical -- Periodicals; 547.2
• DOI: 10.1002/adsc.201801022
• Languages: English
• ISSNs: 1615-4150

Abstract

Abstract: Palladium‐catalyzed β ‐C( sp 3 )‐ H arylation of aliphatic acid derivatives was achieved by means of 2‐dimethylaminoethylamine auxiliary as a directing group. The β ‐C( sp 3 )‐H arylation reactions with aryl and heteroaryl iodides efficiently afforded the corresponding arylated hydrocinnamic acid derivatives. Direct β ‐C( sp 3 )‐H alkynylation, and arene C−H arylation and alkynylation were also realized under the same or slightly modified conditions. The aliphatic diamine auxiliary in the products could be readily removed by methanol in the presence of BF3 ⋅ OEt2 . In comparison with the widely used bidentate nitrogen‐containing directing groups, 2‐dimethylaminoethylamine is a simple, cheap, readily available and removable, and atom‐economical directing group for C−H functionalization. Abstract :