- Synthesis of 2-Amino-1,3-dienes from Propargyl Carbonates via Palladium-Catalyzed Carbon-Nitrogen Bond Formation
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A catalytic method to synthesize 1,3,-dienes from propargylic precursors is reported. This palladium-catalyzed carbon-nitrogen bond-forming reaction furnishes 2-amino-1,3-dienes in excellent yields (up to 98%) and shows a broad tolerance to functional group diversity. The reaction has been demonstrated for over 30 amine substrates, including anilines and indoles, and proceeds under mild neutral conditions. The resulting 1,3-dienes are of great synthetic interest because of their further reaction potential.
- O'Broin, Calvin Q.,Guiry, Patrick J.
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supporting information
p. 879 - 883
(2020/02/04)
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- Palladium-Catalyzed Amidation and Amination of (Hetero)aryl Chlorides under Homogeneous Conditions Enabled by a Soluble DBU/NaTFA Dual-Base System
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The palladium-catalyzed coupling of aryl and heteroaryl chlorides with primary amides under mild homogeneous reaction conditions is reported. Successful C-N coupling is enabled by the use of a unique "dual-base" system consisting of DBU and NaTFA, which serve as proton acceptor and halide scavenger, respectively, using low catalyst loadings (0.5 mol %) with readily available, air-stable palladium precatalysts. The DBU/NaTFA system also enables the room-temperature coupling of primary aryl amines with aryl chlorides and is tolerant of a variety of base-sensitive functional groups.
- Beutner, Gregory L.,Coombs, John R.,Green, Rebecca A.,Inankur, Bahar,Lin, Dong,Qiu, Jun,Roberts, Frederick,Simmons, Eric M.,Wisniewski, Steven R.
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supporting information
p. 1529 - 1537
(2019/09/04)
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- Rhodium-catalyzed electrophilic amination of arylboronic acids with secondary hydroxylamines
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A rhodium(III)-catalyzed electrophilic amination of arylboronic acids with secondary hydroxylamines has been developed. The rhodium catalysis is compatible with heteroarylboronic acids as well as acyl and alkoxycarbonyl protecting groups on the nitrogen of O-acylhydroxylamines, and the corresponding secondary anilines are obtained in good to excellent yields.
- Yasuhisa, Tomohiro,Hirano, Koji,Miura, Masahiro
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supporting information
p. 463 - 465
(2017/04/03)
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- Efficient Friedel–Crafts benzoylation of aniline derivatives with 4-fluorobenzoyl chloride using copper triflate in the synthesis of aminobenzophenones
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ABSTRACT: An efficient pathway for the synthesis of the aminobenzophenone derivatives via Friedel–Crafts benzoylation using copper triflate as catalyst is proposed. New derivatives are synthesized. The copper triflate could be easily recovered and reused without loss of catalytic activity. Both the use of ionic liquids and microwave heating turned out to be fruitful.
- Tran, Phuong Hoang,Phung, Huy Quang,Hansen, Poul Erik,Tran, Hai Ngoc,Le, Thach Ngoc
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p. 893 - 901
(2016/07/06)
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- Reactions of difunctional electrophiles with functionalized aryllithium compounds: Remarkable chemoselectivity by flash chemistry
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Flash chemistry using flow microreactors enables highly chemoselective reactions of difunctional electrophiles with functionalized aryllithium compounds by virtue of extremely fast micromixing. The approach serves as a powerful method for protecting-group-free synthesis using organolithium compounds and opens a new possibility in the synthesis of polyfunctional organic molecules.
- Nagaki, Aiichiro,Imai, Keita,Ishiuchi, Satoshi,Yoshida, Jun-Ichi
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supporting information
p. 1914 - 1918
(2015/02/19)
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- Application of H/D exchange to hydrogen bonding in small molecules
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Do you recognize me? A series of simple amides has been used to demonstrate the application of hydrogen/deuterium exchange in small-molecule hydrogen bonding. By comparison with similar controls, the degree of protection from H/D exchange can provide insight into the degree of hydrogen bonding (see scheme).
- Schneider, Tanya L.,Halloran, Kevin T.,Hillner, Julie A.,Conry, Rebecca R.,Linton, Brian R.
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supporting information
p. 15101 - 15104
(2013/11/06)
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- N,O-Diacyl-4-benzoyl-N-phenylhydroxylamines as photoinduced DNA cleaving agents
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Photoinduced homolytic fission of nitrogen-oxygen bond in N,O-diacyl-4-benzoyl-N-phenylhydroxylamines using ≥310 nm UV light for 10 min produced acylaminyl and acyloxy radicals, which resulted in single strand cleavage of DNA at pH 7.0. Further the DNA cl
- Chowdhury, Nilanjana,Dutta, Sansa,Nishitha, Boda,Dasgupta, Swagata,Singh, N.D. Pradeep
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supporting information; experimental part
p. 5414 - 5417
(2010/12/24)
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- Aminolysis of allyl esters with bislithium aryl amides
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The aminolysis of allyl esters with bislithium amides is reported. Tertiary aryl amides were synthesized in a one-pot reaction with bislithium amides and a suitable electrophile in good yields. The scope of this reaction was demonstrated with a variety of anilines and aminopyridines and applied to the synthesis of triphenylmethylacetamides.
- Faler, Catherine A.,Joullié, Madeleine M.
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p. 7229 - 7231
(2007/10/03)
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- COX-1/COX-2 inhibitors based on the methanone moiety
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This paper focuses on the synthesis and the in vitro testing of dual COX-1/COX-2 inhibitors. Starting from structures of non-steroidal anti-inflammatory drugs (NSAIDs) the diaryl methanone element was chosen as a lead. Modifications were carried out on this scaffold to obtain potent inhibitors of the COX enzymes. The N-(2-aroylphenyl)sulphonamides and -amides were studied in detail, and to consolidate the data evaluated the corresponding 3- and 4-regioisomers were also investigated. The potency and the enzyme selectivity were varied by structural modifications of the lead.
- Dannhardt, Gerd,Fiebich, Bernd L,Schweppenhaeuser, Johannes
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p. 147 - 161
(2007/10/03)
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- (Trichloromethyl)benzene: A versatile reagent for the preparation of substituted benzophenones
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Aromatic and heteroaromatic compounds were benzoylated efficiently with (trichloromethyl)benzene in 1,2-dichloroethane in the presence of aluminium chloride in good yield.
- Ayyanger,Lahoti,Srinivasan,Daniel
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p. 322 - 324
(2007/10/02)
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- SULL'ATTIVITA ANTIFUNGINA FITOIATRICA DI 4-AROILANILIDI
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Some N-acylderivatives of 4-aroylanilines were prepared and tested for phytoiatric antimycotic activity.The substances, most unknown, were subjected to in vitro and in vivo tests (in preventive phase).The compounds studied proved to have interesting activity.
- Massolini, G.,Carmellino, M. L.,Baruffini, A.
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p. 507 - 516
(2007/10/02)
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