58458-85-8Relevant academic research and scientific papers
Access toZ-Selective 1,3-Enynes via Ni-Catalyzed Intermolecular Cross-Alkylalkynylation of Terminal Alkynes
Xiao, Nan,Zhan, Yi-Zhou,Meng, Huan,Shu, Wei
, p. 5186 - 5191 (2021)
Access to 1,3-conjugated enynes with defined stereoselectivity is highly desirable and challenging. Herein, we report a facile synthesis of stereodefined 1,3-conjugated enynes via Ni-catalyzed intermolecular cross-alkylalkynylation of alkynes with unsaturated carbonyl compounds and alkynes or alkynyl silicates. The operational simple protocol proceeds at room temperature and tolerates a wide range of functional groups, providing an attractive alternative to carbonyl-tethered trisubstituted conjugated 1,3-enynes from easily accessible starting materials.
Enantioselective copper-catalyzed remote c(sp3)-h alkynylation of linear primary sulfonamides
Wang, Cheng-Yu,Qin, Zi-Yang,Huang, Yu-Ling,Hou, Yi-Ming,Jin, Ruo-Xing,Li, Chao,Wang, Xi-Sheng
supporting information, p. 4006 - 4009 (2020/05/18)
The highly efficient copper-catalyzed enantioselective alkynylation of the remote C(sp3)-H bond on linear primary sulfonamides is presented here using a radical relay strategy. The chiral box-copper complex, which is used to recapture the in-situ-generated alkyl radical via a 1,5-HAT strategy, is the key to success, affording the chiral alkynes after a following reductive elimination. A general substrate scope, mild conditions, and excellent regio- and enantioselective control are demonstrated in this method.
Enantioselective Trifluoromethylalkynylation of Alkenes via Copper-Catalyzed Radical Relay
Fu, Liang,Zhou, Song,Wan, Xiaolong,Chen, Pinhong,Liu, Guosheng
supporting information, p. 10965 - 10969 (2018/09/11)
A novel enantioselective copper-catalyzed trifluoromethylalkynylation of styrenes, proceeding through a radical relay process, is described herein, which affords structurally diverse CF3-containing propargylic compounds in good yield with excellent enantioselectivities under very mild conditions. In addition, the reaction features wide substrate scope and good functional group tolerance. Moreover, the trifluoromethylalkynylated products can be easily converted into synthetically useful chiral terminal alkynes, allenes, Z-alkenes, as well as CF3-modified nonsteroidal anti-inflammatory drugs.
Dehydrogenative silation, isomerization and the control of syn- vs. anti-addition in the hydrosilation of alkynes
Jun, Chul-Ho,Crabtree, Robert H.
, p. 177 - 187 (2007/10/02)
Alkyne hydrosilation has been examined in detail for the catalysts SbF6 (L = PPh3, bq = 7,8-benzoquinolinato) and RhCl(PPh3)3.Factors that favor the normal syn- or the unusual anti-silane addition to the alkynes are examined.Two other unus
Base cleavage of R-SiMen(OMe)3-n bonds (R m-ClC6H4CH2, PhC, or Cl2CH) and alkoxy exchange in RSiMen(OMe)3-n (R = m-ClC6H4CH2)
Chmielecka, Jadwiga,Chojnowski, Julian,Eaborn, Colin,Stanczyk, Wlodzimierz A.
, p. 1779 - 1784 (2007/10/02)
The rates of cleavage of R-SiMen(OMe)3-n bonds (n = 0-3) in NaOMe-MeOH have been measured for R = (i) -ClC6H4CH2, (ii) Ph, and (iii) Cl2CH.The relative reactivities as n is varied in the sequence 3, 2, 1, 0 within each series are: (i) 1,7.2, 2.7, 0.13; (ii) 1, 27, 24, 5.5; (iii) 1, 38, 93, 29.These reactivity variations are discussed in terms of opposition between the rate-enhancing polar effects of the OMe groups and a unusual type of steric affect which arises on introduction of OMe in place of Me.The rates of replacement of one OMe group of m-ClC6H4CH2Men(OMe)3-n by an OEt group in EtOH containing a base have also been measured; in this case the rates rise progressively with the value of n, the relative reactivities for n = 2,1, and 0 being 1, 4.4, and 27, respectively.
