495414-06-7Relevant articles and documents
Pd(II)-Catalyzed Synthesis of Benzocyclobutenes by β-Methylene-Selective C(sp3)-H Arylation with a Transient Directing Group
Chen, Xiangyang,Hoskin, John F.,Houk, K. N.,Provencher, Philip A.,Sorensen, Erik J.,Wong, Jonathan J.,Yu, Jin-Quan
, p. 20035 - 20041 (2021/12/09)
Methylene-selective C-H functionalization is a significant hurdle that remains to be addressed in the field of Pd(II) catalysis. We report a Pd(II)-catalyzed synthesis of benzocyclobutenes by methylene-selective C(sp3)-H arylation of ketones. The reaction utilizes glycine as a transient directing group and a 2-pyridone ligand, which may govern the methylene selectivity by making intimate molecular associations with the substrate during concerted metalation-deprotonation. This reaction is shown to be highly selective for intramolecular methylene C(sp3)-H arylation, thus enabling sequential C(sp3)-H functionalization.
CuSO4-Catalyzed dual annulation to synthesize O, S or N-containing tetracyclic heteroacenes
Kang, Yan-Biao,Qu, Jian-Ping,Shan, Xiang-Huan,Yang, Bo
, p. 4063 - 4066 (2020/04/20)
In this work, CuSO4 is utilized as a practical redox catalyst for tandem dual annulation in the synthesis of indole-fused tetracyclic heteroacenes, which are important skeletons in both medicinal chemistry and materials chemistry. The preparation of such skeletons in a convenient and efficient manner is in high demand. This method realizes the modular synthesis of benzofuro-, benzothieno-, and indoloindoles from abundant feedstocks such as 2-halobenzyl halides and nitrile derivatives in up to 99% yields, providing a rapid access to diverse indole-fused heteroacenes with biological or optoelectronic properties.
Phenanthroline- tBuOK Promoted Intramolecular C-H Arylation of Indoles with ArI under Transition-Metal-Free Conditions
Shan, Xiang-Huan,Yang, Bo,Zheng, Hong-Xing,Qu, Jian-Ping,Kang, Yan-Biao
, p. 7898 - 7901 (2019/01/04)
The first example of phenanthroline-tBuOK promoted intramolecular radical C-H arylation of N-(2-iodobenzyl)indoles without involvement of transition metals has been developed. A variety of substituted 6H-isoindolo [2, 1-a] indoles were prepared by a simple and efficient intramolecular cyclization using 1,10-phenanthroline in the presence of potassium tert-butoxide and chlorobenzene. This strategy provides a fast and versatile access to isoindolo[2,1-a]indole derivatives for the synthesis of pharmaceuticals and organic electroluminescent (EL) materials.