105364-63-4Relevant academic research and scientific papers
Iron-Catalyzed Tunable and Site-Selective Olefin Transposition
Yu, Xiaolong,Zhao, Haonan,Li, Ping,Koh, Ming Joo
supporting information, p. 18223 - 18230 (2020/12/04)
The catalytic isomerization of C-C double bonds is an indispensable chemical transformation used to deliver higher-value analogues and has important utility in the chemical industry. Notwithstanding the advances reported in this field, there is compelling demand for a general catalytic solution that enables precise control of the C═C bond migration position, in both cyclic and acyclic systems, to furnish disubstituted and trisubstituted alkenes. Here, we show that catalytic amounts of an appropriate earth-abundant iron-based complex, a base and a boryl compound, promote efficient and controllable alkene transposition. Mechanistic investigations reveal that these processes likely involve in situ formation of an iron-hydride species which promotes olefin isomerization through sequential olefin insertion/β-hydride elimination. Through this strategy, regiodivergent access to different products from one substrate can be facilitated, isomeric olefin mixtures commonly found in petroleum-derived feedstock can be transformed to a single alkene product, and unsaturated moieties embedded within linear and heterocyclic biologically active entities can be obtained.
A Simple Nickel Catalyst Enabling an E-Selective Alkyne Semihydrogenation
Thiel, Niklas O.,Kaewmee, Benyapa,Tran Ngoc, Trung,Teichert, Johannes F.
supporting information, p. 1597 - 1603 (2020/02/05)
Stereoselective alkyne semihydrogenations are attractive approaches to alkenes, which are key building blocks for synthesis. With regards to the most atom-economic reducing agent dihydrogen (H2), only few catalysts for the challenging E-selective alkyne semihydrogenation have been disclosed, each with a unique substrate scope profile. Here, we show that a commercially available nickel catalyst facilitates the E-selective alkyne semihydrogenation of a wide variety of substituted internal alkynes. This results in a simple and broadly applicable overall protocol to stereoselectively access E-alkenes employing H2, which could serve as a general method for synthesis.
Using alcohols as simple H2-equivalents for copper-catalysed transfer semihydrogenations of alkynes
Kaicharla, Trinadh,Zimmermann, Birte M.,Oestreich, Martin,Teichert, Johannes F.
supporting information, p. 13410 - 13413 (2019/11/14)
Copper(i)/N-heterocyclic carbene complexes enable a transfer semihydrogenation of alkynes employing simple and readily available alcohols such as isopropanol. The practical overall protocol circumvents the use of commonly employed high pressure equipment when using dihydrogen (H2) on the one hand, and avoids the generation of stoichiometric silicon-based waste on the other hand, when hydrosilanes are used as terminal reductants.
ZrCl2(η-C5Me5)2-AlHCl 2·(THF)2: Efficient hydroalumination of terminal alkynes and cross-coupling of the derived alanes
Andrews, Philip,Latham, Christopher M.,Magre, Marc,Willcox, Darren,Woodward, Simon
supporting information, p. 1488 - 1490 (2013/03/14)
Stabilized AlHCl2·(THF)2 hydroaluminates RCCH with exceptional chemo-, regio- and stereoselectivity under efficient ZrCl 2(η-C5Me5)2 catalysis (2-5 mol%). The resulting vinyl alanes undergo palladium cross-coupling with a wide range of sp2 electrophiles (aryl, heteroaryl and vinyl halides/pseudohalides) in good to excellent yields. The Royal Society of Chemistry 2013.
STUCTURE AND SYNTHESIS OF WF 3681, A NOVEL ALDOSE REDUCTASE INHIBITOR
Uchida, Itsuo,Itoh, Yoshikuni,Namiki, Takayuki,Nishikawa, Motoaki,Hashimoto, Masashi
, p. 2015 - 2018 (2007/10/02)
The structure of WF 3681 (1), an aldose reductase inhibitor isolated from a Chaetomella species, has been determined on the basis of its physical and chemical properties and confirmed by a total synthesis.
