Preparation of (Z)-1,2-dichloroalkenes from terminal alkynes
(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.
Zhou, Ningzhang,Wang, Qiang,Lough, Alan J.,Yan, Hongbin
supporting information; experimental part
p. 625 - 630
(2012/08/08)
Boron trihalide mediated substitution of hydroxyl groups with alkenyl, alkynyl, and allyl moieties
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
Kabalka, George,Borella, Scott,Yao, Min-Liang
p. 325 - 329
(2008/12/21)
Alkenylation of allylic alcohols using alkenylboron dihalides: A formal transition-metal free Suzuki reaction
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.
Kabalka, George W.,Yao, Min-Liang,Borella, Scott,Wu, Zhongzhi
p. 2492 - 2494
(2007/10/03)
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