40597-44-2Relevant academic research and scientific papers
Enantioselective Rhodium(I) Donor Carbenoid-Mediated Cascade Triggered by a Base-Free Decomposition of Arylsulfonyl Hydrazones
Torres, òscar,Parella, Teodor,Solà, Miquel,Roglans, Anna,Pla-Quintana, Anna
, p. 16240 - 16245 (2015)
The reaction of diyne arylsulfonyl hydrazone substrates under rhodium(I)/BINAP catalysis gives access to sulfonated azacyclic frameworks in a highly enantioselective manner. This new cascade process considerably increases the molecular complexity by generating two C-C bonds, one C-S bond, and one C-H bond. Theoretical calculations, competitive experiments, and deuterium labeling have jointly been used to propose a mechanism that accounts for the reaction. The mechanism involves the formation of vinyl rhodium carbenoids, hydride migratory insertion, and intermolecular stereoselective nucleophilic attack. The last two steps are the key to the stereoselectivity of the process.
Phosphine-Catalyzed [3+2] Annulation of β-Sulfonamido-Substituted Enones with Sulfamate-Derived Cyclic Imines
Shi, Wangyu,Zhou, Leijie,Mao, Biming,Wang, Qijun,Wang, Chang,Zhang, Cheng,Li, Xuefeng,Xiao, Yumei,Guo, Hongchao
supporting information, p. 679 - 685 (2019/01/24)
Phosphine-catalyzed [3+2] annulation of β-sulfonamido-substituted enones and sulfamate-derived cyclic imines has been developed, giving a series of imidazoline derivatives in moderate to excellent yields with good to excellent diastereoselectivities. A scale-up reaction worked well under mild reaction conditions. A possible mechanism was proposed on the basis of the results obtained.
A palladium-catalyzed regiocontrollable hydroarylation reaction of allenamides with B2pin2/H2O
Cui, Jie,Meng, Long,Chi, Xiaochen,Liu, Qing,Zhao, Pingping,Zhang, Dao-Peng,Chen, Lei,Li, Xinjin,Dong, Yunhui,Liu, Hui
supporting information, p. 4355 - 4358 (2019/04/26)
A novel palladium-catalyzed regiocontrollable hydroarylation reaction of allenamides with B2pin2/H2O has been disclosed. H2O as an ideal hydrogen source was activated by B2pin2 to furnish allylamines or enamines with a broad functional group tolerance. The regioselectivity for both of the two products was up to 99:1 for most of the examples, which was achieved by adjusting the addition order of the catalyst and iodobenzene derivatives. The tentative investigation of the mechanism proved the reaction to be a non-radical process and the deuterium-labeled experiments indicated that the hydrogen was from H2O.
Palladium-catalyzed intramolecular reductive olefin hydrocarbonation: Benzylic hydrogen serving as a new hydrogen donor
Dong, Xu,Cui, Jie,Song, Jian,Han, Ying,Liu, Qing,Dong, Yunhui,Liu, Hui
supporting information, p. 4903 - 4906 (2017/07/11)
A palladium-catalyzed intramolecular hydrocarbonation of unactivated alkenes was achieved, in which toluene is used as a hydrogen donor for the first time. The radical transfer hydrogenation is designed and realized based on the Bond Dissociation Energy (
Concise synthesis and antiproliferative activity evaluation of ellipticine quinone and its analogs
Nishiyama, Takashi,Hatae, Noriyuki,Mizutani, Masataka,Yoshimura, Teruki,Kitamura, Tsuyoshi,Miyano, Mana,Fujii, Mami,Satsuki, Nanase,Ishikura, Minoru,Hibino, Satoshi,Choshi, Tominari
, p. 1 - 13 (2017/05/05)
We developed a concise protocol for the synthesis of ellipticine quinone from the appropriate 3-iodoindole-2-carbaldehydes in four steps. The key step is the construction of carbazole-1,4-quinone through tandem Ring-Closing Metathesis (RCM) and dehydrogen
An Enantioselective Cascade Cyclopropanation Reaction Catalyzed by Rhodium(I): Asymmetric Synthesis of Vinylcyclopropanes
Torres, òscar,Roglans, Anna,Pla-Quintana, Anna
supporting information, p. 3512 - 3516 (2016/11/25)
N-Tosylhydrazone-yne-ene substrates are satisfactorily prepared and their cyclization under rhodium catalysis is evaluated. A cascade process involving rhodium vinyl carbene formation – through carbene/alkyne metathesis – and cyclopropanation has been dev
Iron-promoted cyclization/halogenation of alkynyl diethyl acetals
Xu, Tongyu,Yu, Zhengkun,Wang, Liandi
supporting information; experimental part, p. 2113 - 2116 (2009/09/28)
FeCl3- and FeBr3-promoted cyclization/halogenation of alkynyl diethyl acetals has been efficiently realized, selectively affording (E)-2-(1-halobenzylidene or alkylidene)-substituted five-membered carbo- and heterocycles which were t
Synthesis of substituted pyridines and pyridazines via ring closing metathesis
Donohoe, Timothy J.,Fishlock, Lisa P.,Basutto, Jose A.,Bower, John F.,Procopiou, Panayiotis A.,Thompson, Amber L.
supporting information; experimental part, p. 3008 - 3010 (2009/12/01)
RCM can be used to make aromatic heterocycles, namely pyridines and, for the first time, pyridazines; the key step after RCM involves elimination of sulfinate to provide the aromatic system. The Royal Society of Chemistry 2009.
Concise stereocontrolled formal synthesis of (±)-quinine and total synthesis of (±)-7-hydroxyquinine via merged Morita-Baylis-Hillman-Tsuji- Trost cyclization
Webber, Peter,Krische, Michael J.
supporting information; experimental part, p. 9379 - 9387 (2009/04/06)
(Chemical Equation Presented) Concise stereoselective syntheses of (±)-quinine and (±)-7-hydroxyquinine are achieved using a catalytic enone cycloallylation that combines the nucleophilic features of the Morita-Baylis-Hillman reaction and the electrophili
Impurity annihilation; a strategy for solution phase combinatorial chemistry with minimal purification
Barrett, Anthony G. M.,Smith, Marie L.,Zecri, Frederic J.
, p. 2317 - 2318 (2007/10/03)
The selective annihilation of all contaminants in the solution phase formation of amides or sulfonamides is accomplished by their incorporation into a polyurea and removal by filtration.
