ChemInform Abstract: Nickel-Catalyzed Cross-Coupling of Aryl Bromides with Tertiary Grignard Reagents Utilizing Donor-Functionalized N-Heterocyclic Carbenes (NHCs).

ChemInform ◽  
2011 ◽  
Vol 42 (40) ◽  
pp. no-no
Author(s):  
Claudia Lohre ◽  
Thomas Droege ◽  
Congyang Wang ◽  
Frank Glorius
Keyword(s):  
Cross Coupling ◽  
Heterocyclic Carbenes ◽  
Grignard Reagents ◽  
Aryl Bromides

ChemInform Abstract: N-Heterocyclic Carbenes. Part 27. Nickel-Catalyzed Cross-Coupling of Aryl Chlorides with Aryl Grignard Reagents.

ChemInform ◽  
2010 ◽  
Vol 31 (30) ◽  
pp. no-no
Author(s):  
Volker P. W. Boehm ◽  
Thomas Weskamp ◽  
Christian W. K. Gstoettmayr ◽  
Wolfgang A. Herrmann
Keyword(s):  
Cross Coupling ◽  
Heterocyclic Carbenes ◽  
Grignard Reagents ◽  
Aryl Chlorides

Cobalt-catalyzed Cross-coupling Reactions of Aryl Bromides with Alkyl Grignard Reagents

2008 ◽  
Vol 37 (11) ◽  
pp. 1178-1179 ◽  
Author(s):  
Hiroyuki Hamaguchi ◽  
Minoru Uemura ◽  
Hiroto Yasui ◽  
Hideki Yorimitsu ◽  
Koichiro Oshima
Keyword(s):  
Cross Coupling ◽  
Grignard Reagents ◽  
Coupling Reactions ◽  
Cross Coupling Reactions ◽  
Aryl Bromides

ChemInform Abstract: Cobalt-Catalyzed Cross-Coupling Reactions of Aryl Bromides with Alkyl Grignard Reagents.

ChemInform ◽  
2009 ◽  
Vol 40 (15) ◽  
Author(s):  
Hiroyuki Hamaguchi ◽  
Minoru Uemura ◽  
Hiroto Yasui ◽  
Hideki Yorimitsu ◽  
Koichiro Ohsima
Keyword(s):  
Cross Coupling ◽  
Grignard Reagents ◽  
Coupling Reactions ◽  
Cross Coupling Reactions ◽  
Aryl Bromides

Fe-Catalyzed Conjunctive Cross-Couplings of Unactivated Alkenes with Grignard Reagents

2020 ◽  
Author(s):  
Lei Liu ◽  
Wes Lee ◽  
Cassandra R. Youshaw ◽  
Mingbin Yuan ◽  
Michael B. Geherty ◽  
...  
Keyword(s):  
Functional Groups ◽  
Cross Coupling ◽  
Alkyl Halides ◽  
Grignard Reagents ◽  
Turnover Frequency ◽  
Diverse Range ◽  
Cascade Cyclization ◽  
Radical Cascade

The first iron-catalyzed three-component cross-coupling of unactivated olefins with alkyl halides and Grignard reagents is reported. The reaction operates under fast turnover frequency and tolerates a diverse range of sp2-hybridized nucleophiles, alkyl halides, and unactivated olefins bearing diverse functional groups to yield the desired 1,2-alkylarylated products with high regiocontrol. Further, we demonstrate that this protocol is amenable for the synthesis of new (hetero)carbocycles including tetrahydrofurans and pyrrolidines via a three-component radical cascade cyclization/arylation that forges three new C-C bonds.

Design and Development of Fe-Catalyzed Intra- and Intermolecular Carbofunctionalization of Vinyl Cyclopropanes

2019 ◽  
Author(s):  
Lei Liu ◽  
Wes Lee ◽  
Mingbin Yuan ◽  
Chris Acha ◽  
Michael B. Geherty ◽  
...  
Keyword(s):  
Bond Formation ◽  
Cross Coupling ◽  
Alkyl Halides ◽  
Grignard Reagents ◽  
Mechanistic Studies ◽  
Radical Intermediates ◽  
Design And Implementation ◽  
Solvent Cage ◽  
Radical Cascade ◽  
Radical Processes

Design and implementation of the first (asymmetric) Fe-catalyzed intra- and intermolecular difunctionalization of vinyl cyclopropanes (VCPs) with alkyl halides and aryl Grignard reagents has been realized via a mechanistically driven approach. Mechanistic studies support the diffusion of the alkyl radical intermediates out of the solvent cage to participate in an intra- or -intermolecular radical cascade with the VCP followed by re-entering the Fe radical cross-coupling cycle to undergo selective C(sp2)-C(sp3) bond formation. Overall, we provide new design principles for Fe-mediated radical processes and underscore the potential of using combined computations and experiments to accelerate the development of challenging transformations.

Monodentate Trialkylphosphines: Privileged Ligands in Metal-catalyzed Crosscoupling Reactions

2020 ◽  
Vol 24 (3) ◽  
pp. 231-264 ◽  
Author(s):  
Kevin H. Shaughnessy
Keyword(s):  
Transition Metal ◽  
Cross Coupling ◽  
Coupling Reactions ◽  
Cross Coupling Reactions ◽  
Aryl Bromides ◽  
Wide Range ◽  
Sterically Demanding ◽  
Transition Metal Catalyzed ◽  
Catalyzed Reactions ◽  
Metal Catalyzed

Phosphines are widely used ligands in transition metal-catalyzed reactions. Arylphosphines, such as triphenylphosphine, were among the first phosphines to show broad utility in catalysis. Beginning in the late 1990s, sterically demanding and electronrich trialkylphosphines began to receive attention as supporting ligands. These ligands were found to be particularly effective at promoting oxidative addition in cross-coupling of aryl halides. With electron-rich, sterically demanding ligands, such as tri-tertbutylphosphine, coupling of aryl bromides could be achieved at room temperature. More importantly, the less reactive, but more broadly available, aryl chlorides became accessible substrates. Tri-tert-butylphosphine has become a privileged ligand that has found application in a wide range of late transition-metal catalyzed coupling reactions. This success has led to the use of numerous monodentate trialkylphosphines in cross-coupling reactions. This review will discuss the general properties and features of monodentate trialkylphosphines and their application in cross-coupling reactions of C–X and C–H bonds.

scholarly journals Microwave-assisted Efficient Synthesis of Alliodorin and (±)-Curcuhydroquinone

1999 ◽  
Vol 23 (2) ◽  
pp. 164-165
Author(s):  
Goverdhan L. Kad ◽  
Anupam Khurana ◽  
Vasundhara Singh ◽  
Jasvinder Singh
Keyword(s):  
Grignard Reagents ◽  
Methyl Groups ◽  
Efficient Synthesis ◽  
Alkyl Aryl ◽  
Microwave Assisted ◽  
Aryl Bromides ◽  
Key Steps

Terpenoids 1 and 2 have been synthesized from readily available starting materials using Li2CuCI4-catalysed coupling of Grignard reagents with alkyl/aryl bromides and microwave-assisted oxidation of allylic methyl groups, using SeO2/ButOOH adsorbed over SiO2 as key steps.

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