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A Simple Aliphatic Diamine Auxiliary for Palladium‐Catalyzed Arylation of Unactivated β‐C(sp3)‐H Bonds
Advanced Synthesis & Catalysis ( IF 5.4 ) Pub Date : 2018-10-16 , DOI: 10.1002/adsc.201801022
Jiang Lou 1, 2 , Quannan Wang 1, 2 , Yuan He 1, 2 , Zhengkun Yu 1, 3
Affiliation  

Palladium‐catalyzed β‐C(sp3)H arylation of aliphatic acid derivatives was achieved by means of 2‐dimethylaminoethylamine auxiliary as a directing group. The β‐C(sp3)‐H arylation reactions with aryl and heteroaryl iodides efficiently afforded the corresponding arylated hydrocinnamic acid derivatives. Direct β‐C(sp3)‐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.

中文翻译:

钯催化未活化的β-C(sp3)-H键的简单脂肪族二胺助剂

钯催化的β -C(SP 3- H为通过2-二甲基氨基乙胺辅作为定向基团来实现的脂族酸衍生物的芳基化。的β -C(SP 3与芳基和杂芳基碘化物)-H的芳基化反应有效地得到相应的芳基化的氢化肉桂酸衍生物。在相同或稍加修饰的条件下,也可以实现直接的β- C(sp 3)-H炔基化,芳烃CH芳基化和炔基化。在产品中的脂肪族二胺的辅助可通过甲醇容易地除去在BF的存在3  ⋅OET 2。与广泛使用的双齿含氮指导基团相比,2-二甲基氨基乙胺是一种简单,便宜,易于获得且可移动的,经济的CH-H官能团指导基团。
更新日期:2018-10-16
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