1-chloro-4-(3,5-dichloropent-1-ynyl)benzene

1-chloro-4-(3,5-dichloropent-1-ynyl)benzene (3ci) :

Following general procedure, The product was purified by flash column chromatography on silica gel (petroleum ether) and 1c : 2i = 1:53, obtained in 61 % yield as a pale yellow oil (29.9 mg).

1H NMR (600 MHz, CDCl3) δ 7.37 (t, J = 10.3 Hz, 2H), 7.31 (d, J = 8.2 Hz, 2H), 5.00 (t, J = 6.8 Hz, 1H), 3.78 (ddd, J = 16.9, 10.1, 4.7 Hz, 2H), 2.47 (q, J = 6.5 Hz, 2H).

13C NMR (151 MHz, CDCl3) δ 135.1, 133.0, 128.7, 120.2, 86.9, 85.6, 45.9, 41.4, 40.8.

HRMS calcd for C11H9Cl3 [M + H]+ 245.9770; found: 245.9772.

Directed alkynylation of unactivated C(sp3)-H bonds with ethynylbenziodoxolones mediated by DTBP

Green Chem., 2016, 18,4185-4188

DOI: 10.1039/C6GC01336H, Communication

Zhi-Fei Cheng, Yi-Si Feng, Chun Rong, Tao Xu, Peng-Fei Wang, Jun Xu, Jian-Jun Dai, Hua-Jian Xu
A general and efficient alkynylation of unactivated C(sp³)-H bonds under metal-free conditions was developed herein.

Directed alkynylation of unactivated C(sp³)–H bonds with ethynylbenziodoxolones mediated by DTBP

Zhi-Fei Cheng,^a   Yi-Si Feng,*^abc   Chun Rong,^a   Tao Xu,^a  Peng-Fei Wang,^a   Jun Xu,^a   Jian-Jun Dai^a and   Hua-Jian Xu*^abc  

*Corresponding authors

^aSchool of Chemistry and Chemical Engineering, School of Biological and Medical Engineering, Hefei University of Technology, Hefei 230009, P. R. China

^bAnhui Key Laboratory of Controllable Chemical Reaction and Material Chemical Engineering, Hefei 230009, P. R. China
E-mail: hjxu@hfut.edu.cn
Fax: (+86)-551-62904405

^cAnhui Provincial Laboratory of Heterocyclic Chemistry, Maanshan 243110, China

Green Chem., 2016,18, 4185-4188

DOI: 10.1039/C6GC01336H, http://pubs.rsc.org/en/Content/ArticleLanding/2016/GC/C6GC01336H?utm_source=feedburner&utm_medium=feed&utm_campaign=Feed%3A+rss%2FGC+%28RSC+-+Green+Chem.+latest+articles%29#!divAbstract

A general and efficient method for the direct alkynylation of unactivated C(sp³)–H bonds under metal-free conditions is described. The reaction performs smoothly under mild conditions and shows excellent functional-group tolerance. Initial mechanistic investigation indicates that the reaction may involve a radical pathway.

 

//////////Directed alkynylation, unactivated C(sp3)-H bonds,  ethynylbenziodoxolones,  DTBP