51246-14-1Relevant academic research and scientific papers
Arylethyne bromoboration-Negishi coupling route to E- Or Z-aryl-substituted trisubstituted alkenes of ≥ 98% isomeric purity. New horizon in the highly selective synthesis of trisubstituted alkenes
Wang, Chao,Xu, Zhaoqing,Tobrman, Tomas,Negishi, Ei-Ichi
supporting information; experimental part, p. 627 - 631 (2010/06/21)
The hitherto unprecedented palladiumcatalyzed cross-coupling of (Z)-β-bromo-β-arylethenylboranes can be made to proceed satisfactorily through (1) the use of highly catalytically active bis(tri-tert-butylphosphine) palladium or dichloro[N,N-bis-(2,6-diisopropylphenyl)imidazol-2-yl](m- chloropyridine)palladium and (2) conversion of the dibromoboryl group to the (pinacol)boryl group. Thus, a wide variety of carbon groups can be used to substitute bromine in ≥ 98% stereo- and regioselectivity, while suppressing the otherwise dominant β-debromoboration. Together with the alkylethyne-based protocols, the alkyne bromoboration-Negishi coupling tandem process has emerged as the most widely applicable and highly selective route to trisubstituted alkenes including those that are otherwise difficult to access.
Rh(i)-catalyzed formal [2+2+2] cycloadditions of 1,6-diynes with potassium (Z)-(2-bromovinyl)trifluoroborate: A new strategy and a facile entry to polysubstituented benzene derivatives
Fang, Xianjie,Sun, Junyao,Tong, Xiaofeng
supporting information; experimental part, p. 3800 - 3802 (2010/08/07)
A new strategy for Rh(i)-catalyzed [2+2+2] cycloadditions of 1,6-diynes with potassium (Z)-(2-bromovinyl)trifluoroborate as the third two-atom unit has been realized, which provides a facile entry to polysubstituented benzene derivatives.
Identification of a boron-containing intermediate in the boron tribromide mediated aryl propargyl ether cleavage reaction
Yao, Min-Liang,Reddy, Marepally Srinivasa,Zeng, Wenbin,Hall, Kelly,Walflsh, Ingrid,Kabalka, George W.
supporting information; experimental part, p. 1385 - 1387 (2009/07/04)
An alternate reaction mechanism for the boron tribromide mediated deprotection of aryl propargyl ethers based on the isolation of a key boron-containing byproduct is proposed. On the basis of the new mechanistic insight, we discovered that HBBr2 · SMe2 can also be used for cleaving aryl propargyl ethers.
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.
