51246-11-8Relevant academic research and scientific papers
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.
Boron trihalide mediated substitution of hydroxyl groups with alkenyl, alkynyl, and allyl moieties
Kabalka, George,Borella, Scott,Yao, Min-Liang
, p. 325 - 329 (2008/12/21)
The coupling of alcohols with alkenyl- and alkynylboron dihalides with high olefin stereoselectivity is described. The reaction provides a facile route to internal acetylenes. Notably, the allylation of propargylic alcohols mediated by boron trichloride p
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.
