18322-82-2Relevant articles and documents
Selecting double bond positions with a single cation-responsive iridium olefin isomerization catalyst
Camp, Andrew M.,Kita, Matthew R.,Blackburn, P. Thomas,Dodge, Henry M.,Chen, Chun-Hsing,Miller, Alexander J.M.
supporting information, p. 2792 - 2800 (2021/03/01)
The catalytic transposition of double bonds holds promise as an ideal route to alkenes of value as fragrances, commodity chemicals, and pharmaceuticals; yet, selective access to specific isomers is a challenge, normally requiring independent development of different catalysts for different products. In this work, a single cation-responsive iridium catalyst selectively produces either of two different internal alkene isomers. In the absence of salts, a single positional isomerization of 1-butene derivatives furnishes 2-alkenes with exceptional regioselectivity and stereoselectivity. The same catalyst, in the presence of Na+, mediates two positional isomerizations to produce 3-alkenes. The synthesis of new iridium pincer-crown ether catalysts based on an aza-18-crown-6 ether proved instrumental in achieving cation-controlled selectivity. Experimental and computational studies guided the development of a mechanistic model that explains the observed selectivity for various functionalized 1-butenes, providing insight into strategies for catalyst development based on noncovalent modifications.
Asymmetric cross-coupling of potassium 2-butenyltrifluoroborates with aryl and 1-alkenyl bromides catalyzed by a Pd(OAc)2/Josiphos complex
Yamamoto, Yasunori,Takada, Shingo,Miyaura, Norio
, p. 1368 - 1369 (2007/10/03)
The asymmetric cross-coupling reaction of [CH3CH= CHCH 2BF3]K with aryl or 1-alkenyl bromides selectively occurred at the γ-carbon of 2-butenylborane moiety with regioselectivities in a range of 84-99%. The enantioselectiv
α-Selective cross-coupling reaction of allyltrifluorosilanes: Remarkable ligand effect on the regiochemistry
Hatanaka, Yasuo,Goda, Ken-Ichi,Hiyama, Tamejiro
, p. 6511 - 6514 (2007/10/02)
The cross-coupling reaction of allyltrifluorosilanes with aryl halides or aryl triflates promoted by a fluoride salt takes place at the α-carbon of the allyltrifluorosilanes in the presence of a catalytic amount of PdCl2[Ph2P(CH
