2632-70-4Relevant academic research and scientific papers
One-pot Negishi cross-coupling reaction of aryldiazonium salts via Ni catalysis induced by visible-light
Wang, Lianjun,Liu, Gao
, (2019/08/29)
Visible-light induced catalysis is of high interest for its mild and environmentally benign properties. Herein, a general Ni catalysis accelerated by visible-light was successfully developed for one-pot Negishi coupling reactions at room temperature in a short reaction time (2Zn generated in situ from Grignard reagents and ZnBr2. This protocol provides a convenient access to C–C bond formation for important biaryl components. It tolerates various functional groups, and Hammett study illuminates the possiblility of Ni(III)/Ni(I) redox catalytic cycle.
Exploiting Synergistic Effects in Organozinc Chemistry for Direct Stereoselective C-Glycosylation Reactions at Room Temperature
Hernán-Gómez, Alberto,Orr, Samantha A.,Uzelac, Marina,Kennedy, Alan R.,Barroso, Santiago,Jusseau, Xavier,Lemaire, Sébastien,Farina, Vittorio,Hevia, Eva
supporting information, p. 10630 - 10634 (2018/08/01)
Pairing a range of bis(aryl) zinc reagents ZnAr2 with the stronger Lewis acidic [(ZnArF2)] (ArF=C6F5), enables highly stereoselective cross-coupling between glycosyl bromides and ZnAr2 without the use of a transition metal. Reactions occur at room temperature with excellent levels of stereoselectivity, where ZnArF2 acts as a non-coupling partner although its presence is crucial for the execution of the C(sp2)–C(sp3) bond formation process. Mechanistic studies have uncovered a unique synergistic partnership between the two zinc reagents, which circumvents the need for transition-metal catalysis or forcing reaction conditions. Key to the success of the coupling is the avoidance of solvents that act as Lewis bases versus diarylzinc compounds (e.g. THF).
Decarboxylative Negishi Coupling of Redox-Active Aliphatic Esters by Cobalt Catalysis
Liu, Xu-Ge,Zhou, Chu-Jun,Lin,Han, Xiang-Lei,Zhang, Shang-Shi,Li, Qingjiang,Wang, Honggen
supporting information, p. 13096 - 13100 (2018/09/21)
A cobalt-catalyzed decarboxylative Negishi coupling reaction of redox-active aliphatic esters with organozinc reagents was developed. The method enabled efficient alkyl–aryl, alkyl–alkenyl, and alkyl–alkynyl coupling reactions under mild reaction conditions with no external ligand or additive needed. The success of an in situ activation protocol and the facile synthesis of the drug molecule (±)-preclamol highlight the synthetic potential of this method. Mechanistic studies indicated that a radical mechanism is involved.
Alkyl?(Hetero)Aryl Bond Formation via Decarboxylative Cross-Coupling: A Systematic Analysis
Sandfort, Frederik,O'Neill, Matthew J.,Cornella, Josep,Wimmer, Laurin,Baran, Phil S.
supporting information, p. 3319 - 3323 (2017/03/17)
Suzuki, Negishi, and Kumada couplings are some of the most important reactions for the formation of skeletal C?C linkages. Their widespread use to forge bonds between two aromatic rings has enabled every branch of chemical science. The analogous union between alkyl halides and metallated aryl systems has not been as widely employed due to the lack of commercially available halide building blocks. Redox-active esters have recently emerged as useful surrogates for alkyl halides in cross-coupling chemistry. Such esters are easily accessible through reactions between ubiquitous carboxylic acids and coupling agents widely used in amide bond formation. This article features an amalgamation of in-house experience bolstered by approximately 200 systematically designed experiments to accelerate the selection of ideal reaction conditions and activating agents for the cross-coupling of primary, secondary, and tertiary alkyl carboxylic acids with both aryl and heteroaryl organometallic species.
Copper-Catalyzed Negishi Coupling of Diarylzinc Reagents with Aryl Iodides
Thapa, Surendra,Vangala, Adarsh S.,Giri, Ramesh
, p. 504 - 511 (2016/02/14)
We report an efficient copper(I) iodide catalyzed cross-coupling of diarylzinc reagents with aryl iodides. The reaction proceeds under ligand-free conditions at low catalyst loading (5 mol%) and tolerates a variety of functional groups.
Direct C-C bond construction from arylzinc reagents and aryl halides without external catalysts
Minami, Hiroki,Wang, Xuan,Wang, Chao,Uchiyama, Masanobu
supporting information, p. 7891 - 7894 (2014/01/06)
Direct cross-coupling between an arylzinc reagent and an aryl halide was accomplished without any external catalyst, enabling efficient and selective formation of the corresponding biaryl compound with broad functional group compatibility. Direct cross-coupling between a diarylzinc compound and an aryl iodide was accomplished without using any external catalyst. The reaction is efficient and selective, enabling formation of the corresponding biaryl compounds with broad functional group compatibility. The reaction is proposed to proceed by a thermally initiated single electron transfer (SET) route. Copyright
