38350-29-7Relevant academic research and scientific papers
Synthesis of Enantioenriched 3,4-Disubstituted Chromans through Lewis Base Catalyzed Carbosulfenylation
Denmark, Scott E.,Laverny, Aragorn,Menard, Travis
, p. 14290 - 14310 (2021/11/12)
A method for the catalytic, enantioselective, carbosulfenylation of alkenes to construct 3,4-disubstituted chromans is described. Alkene activation proceeds through the intermediacy of enantioenriched, configurationally stable thiiranium ions generated from catalytic, Lewis base activation of an electrophilic sulfenylating agent. The transformation affords difficult-to-generate, enantioenriched, 3,4-disubstituted chromans in moderate to high yields and excellent enantioselectivities. A variety of substituents are compatible including electronically diverse functional groups as well as several functional handles such as aryl halides, esters, anilines, and phenols. The resulting thioether moiety is amenable to a number of functional group manipulations and transformations. Notably, the pendant sulfide was successfully cleaved to furnish a free thiol which readily provides access to most sulfur-containing functional groups which are present in natural products and pharmaceuticals.
Homogeneous Pd-catalyzed transformation of terminal alkenes into primary allylic alcohols and derivatives
Tomita, Ren,Mantani, Kohei,Hamasaki, Akiyuki,Ishida, Tamao,Tokunaga, Makoto
supporting information, p. 9914 - 9917 (2014/08/18)
Synthesis of primary alcohols from terminal alkenes is an important process in both bulk and fine chemical syntheses. Herein, a homogeneous Pd-complex-catalyzed transformation of terminal alkenes into primary allylic alcohols, by using 5 mol % [Pd(PPh3)4] as a catalyst, and H2O, CO2, and quinone derivatives as reagents, is reported. When alcohols were used instead of H2O, allylic ethers were obtained. A proposed mechanism includes the addition of oxygen nucleophiles at the less-hindered terminal position of π-allyl Pd intermediates.
An efficient palladium-catalyzed synthesis of cinnamyl ethers from aromatic halides, phenols, and allylic chloride
Wang, Wei,Zhou, Rong,Jiang, Zhi-Jie,Wang, Kun,Fu, Hai-Yan,Zheng, Xue-Li,Chen, Hua,Li, Rui-Xiang
, p. 616 - 622 (2014/05/20)
A one-pot, two-step catalytic protocol for the preparation of cinnamyl ethers from simple and readily available aryl halides, phenols and allyl chloride is reported for the first time. This simple and highly efficient palladium nanoparticles catalytic system shows good regio- and stereoselectivities and affords the desired products in good to high yields (49-85%) from aryl iodides. Furthermore, less reactive aryl bromides can also give the cinnamyl ethers in moderate yields (24-72%).
Copper-catalyzed decarboxylative C(sp2)-C(sp3) coupling reactions via radical mechanism
Yang, Hailong,Sun, Peng,Zhu, Yan,Yan, Hong,Lu, Linhua,Qu, Xiaoming,Li, Tingyi,Mao, Jincheng
supporting information; experimental part, p. 7847 - 7849 (2012/09/05)
We have successfully developed an example of copper-catalyzed decarboxylative C(sp2)-C(sp3) coupling reactions via C-H functionalization for the first time. It is noteworthy that our catalytic system is very stable, low-cost, palladium-free, ligand-free, and easily accessible.
Palladium-catalyzed Mizoroki-Heck reaction of allyl aryl ethers with aryl iodides using phosphine-free hydrazone ligands
Mino, Takashi,Shindo, Hiroaki,Kaneda, Tomoko,Koizumi, Tomoko,Kasashima, Yoshio,Sakamoto, Masami,Fujita, Tsutomu
experimental part, p. 5358 - 5360 (2009/12/06)
Palladium-catalyzed Mizoroki-Heck reaction of allyl aryl ethers with aryl iodides gave aryl cinnamyl ethers using a catalytic amount of Pd(OAc)2 in DMF at 50 °C with phosphine-free hydrazone as a ligand in good yields.
Regio- and enantioselective iridium-catalyzed intermolecular allylic etherification of achiral allylic carbonates with phenoxides
Lopez, Fernando,Ohmura, Toshimichi,Hartwig, John F.
, p. 3426 - 3427 (2007/10/03)
An enantioselective and regioselective iridium-catalyzed allylic etherification is described. The reaction of sodium and lithium aryloxides with achiral (E)-cinnamyl and terminal aliphatic allylic electrophiles in the presence of 2 mol % of an iridium-phosphoramidite complex provides chiral allylic aryl ethers in high yields and excellent levels of regio- and enantioselectivity. Lithium aryloxides containing a single substituent at an ortho, meta, or para position as well as sterically hindered phenoxides were tolerated. Reactions in THF displayed the most suitable balance of rate, regio-, and enantioselectivity. High ee's were also observed for the products from the reaction of alkyl (E)-allylic carbonates. Copyright
