51246-11-8Relevant articles and documents
Preparation of (Z)-1,2-dichloroalkenes from terminal alkynes
Zhou, Ningzhang,Wang, Qiang,Lough, Alan J.,Yan, Hongbin
supporting information; experimental part, p. 625 - 630 (2012/08/08)
(Z)-1,2-Dihaloalkenes are thermodynamically disfavoured of the two stereoisomers. This paper reports the synthesis of some (Z)-1,2-dichloroalkene analogues from mucochloric acid. A more versatile approach involved the chloroboration of terminal alkynes to yield corresponding (Z)-chloroboronic acid as a first step. Treatment of the organoboronic acid with potassium hydrogen difluoride followed by tetrabutylammonium trichloride gave (Z)-1,2- dichloroalkenes in moderate to good yields in a stereospecific manner.
Alkenylation of allylic alcohols using alkenylboron dihalides: A formal transition-metal free Suzuki reaction
Kabalka, George W.,Yao, Min-Liang,Borella, Scott,Wu, Zhongzhi
, p. 2492 - 2494 (2007/10/03)
Carbon-carbon bond formation via substitution of an allylic hydroxide with stereodefined alkenyl groups using alkenylboron dihalides in the absence of transition metals. The Royal Society of Chemistry 2005.