7399-52-2Relevant academic research and scientific papers
Phenyl substitution effects on rate acceleration of cation radical deazetation of 2,3-diazabicyclo[2.2.2]oct-2-enes
Ikeda,Minegishi,Takahashi,Miyashi
, p. 4377 - 4380 (1996)
Under the 9,10-dicyanoanthracene (DCA)-photosensitized electron-transfer conditions 1-phenyl-2,3-diazabicyclo[2.2.2]oct-2-ene (1b) and 1,4-diphenyl- 2,3-diazabicyclo[2.2.2]oct-2-ene (1c) were deazetized with rate constants, k(-N2), of ca. 8.4 x 107/
Nickel-Catalyzed Hydrosilylation of Terminal Alkenes with Primary Silanes via Electrophilic Silicon-Hydrogen Bond Activation
Wu, Xiaoyu,Ding, Guangni,Lu, Wenkui,Yang, Liqun,Wang, Jingyang,Zhang, Yuxuan,Xie, Xiaomin,Zhang, Zhaoguo
, p. 1434 - 1439 (2021/02/16)
We report a simple and effective nickel-based catalytic system, NiCl2·6H2O/tBuOK, for the electrophilically activated hydrosilylation of terminal alkenes with primary silanes. This protocol provides excellent performance under mild reaction conditions: ex
Visible-Light-Induced Meerwein Fluoroarylation of Styrenes
Tang, Hai-Jun,Zhang, Bin,Xue, Fei,Feng, Chao
supporting information, p. 4040 - 4044 (2021/05/26)
An unprecedented approach for assembling a broad range of 1,2-diarylethane derivatives with fluorine-containing fully substituted carbon centers was developed. The protocol features straightforward operation, proceeds under metal-free condition, and accommodates a large variety of synthetically useful functionalities. The critical aspect to the success of this novel transformation lies in using aryldiazonium salts as both aryl radical progenitor and also as single electron acceptor which elegantly enables a radical-polar crossover manifold.
Palladium-Catalyzed Hydrocarbonylative Cyclization of 1,5-Dienes
Zou, Suchen,Gao, Bao,Huang, Yao,Zhang, Tianze,Huang, Hanmin
, p. 6333 - 6336 (2019/08/26)
A novel and atom-economic palladium-catalyzed isomerization-hydrocarbonylative cyclization reaction of 1,5-dienes to 2-alkylidenecyclopentanones has been developed, which provides a rapid and straightforward approach to 2-alkylidenecyclopentanones with high stereoselectivity. The reaction was found to proceed via alkene isomerization and selective hydrocarbonylative cyclization to generate 2-alkylidenecyclopentanones with high selectivity.
Regioselective Transfer Hydrodeuteration of Alkenes with a Hydrogen Deuteride Surrogate Using B(C6F5)3 Catalysis
Walker, Johannes C. L.,Oestreich, Martin
, p. 6411 - 6414 (2018/10/20)
A regioselective hydrodeuteration of alkenes using monodeuterated cyclohexa-1,4-dienes as surrogates for hydrogen deuteride (HD) gas is reported. The metal-free process proceeds under B(C6F5)3 catalysis presumably by deuteride abstraction to form borodeuteride [DB(C6F5)3]a and highly Br?nsted-acidic Wheland intermediates. Low catalyst loadings (2.5 mol %) are used, and the reaction proceeds at room temperature.
Asymmetric Synthesis of Chiral Cyclopentanes Bearing an All-Carbon Quaternary Stereocenter by Zirconium-Catalyzed Double Carboalumination
Xu, Shiqing,Wang, Chuan,Komiyama, Masato,Tomonari, Yasuhiko,Negishi, Ei-Ichi
supporting information, p. 11502 - 11505 (2017/09/11)
Herein, we report a zirconium-catalyzed enantio- and diastereoselective inter/intramolecular double carboalumination of unactivated 2-substituted 1,5-dienes, which provides efficient and direct access to chiral cyclopentanes through the generation of two
Double-Chelation-Assisted Rh-Catalyzed Intermolecular Hydroacylation between Salicylaldehydes and 1,4-Penta- or 1,5-Hexadienes
Imai, Masanori,Tanaka, Masakazu,Tanaka, Keitaro,Yamamoto, Yoichiro,Imai-Ogata, Naoko,Shimowatari, Masato,Nagumo, Shinji,Kawahara, Norio,Suemune, Hiroshi
, p. 1144 - 1150 (2007/10/03)
Intermolecular hydroacylation between salicylaldehydes 1, 26-40 and 1,4-penta- or 1,5-hexadienes 4-13 by Rh-catalyst proceeded under mild reaction conditions to give a mixture of iso- and normal-hydroacylated products 14-25, 41-55, and 57-60. In the hydroacylation reaction, chelation of both salicylaldehyde and diene to the Rh-complex plays a crucial role. The ratio of iso- and normal-hydroacylated products could be regulated by the addition of salicylic acid or amines. The effects of various Rh-complexes, solvents, and additives were examined, and the plausible mechanisms of the catalytic cycle were proposed on the basis of the deuterium-labeling salicylaldehyde experiments.
Double-chelation-assisted Rh-catalyzed intermolecular hydroacylation
Tanaka, Masakazu,Imai, Masanori,Yamamoto, Yoichiro,Tanaka, Keitaro,Shimowatari, Masato,Nagumo, Shinji,Kawahara, Norio,Suemune, Hiroshi
, p. 1365 - 1367 (2007/10/03)
(Matrix presented) Rh-Catalyzed intermolecular hydroacylation between salicylaldehydes and 1,5-hexadienes proceeded under remarkably mild reaction conditions to afford a mixture of iso- and normal-hydroacylated products in good yields. The experiments using deuterated salicylaldehyde-d revealed that "double chelation" of salicylaldehyde and 1,5-hexadiene to Rh-complex played vital roles in the catalytic cycle of intermolecular hydroacylation.
Photolysis of Reluctant Azoalkanes. Effect of Structure on Photochemical Loss of Nitrogen from 2,3-Diazabicyclooct-2-ene Derivatives
Engel, Paul S.,Horsey, Douglas W.,Keys, Dalen E.,Nalepa, Christopher J.,Soltero, Luis R.
, p. 7108 - 7114 (2007/10/02)
Azoalkanes containing the bicycloskeleton often prove to be remarkable stable toward loss of nitrogen.These derivatives of 2,3-diazabicyclooct-2-ene (DBO) also exhibit fluorescence whose lifetime extends to 600 ns.This paper is an attempt to understand the effect of fused rings and bridgehead substituents on the photochemical and photophysical properties of DBO.The main factor controlling quantum yields of nitrogen is a 6-11 kcal mol-1 activation barrier that differs for the singlet and triplet states and that seems to mimic the barrier to ground-state deazatization.The product distribution for DBO derivatives is rationalized on the basis of interconverting singlet 1,4-biradicaloids.
