282727-20-2Relevant articles and documents
Rhodium-Catalyzed Addition of Organozinc Iodides to Carbon-11 Isocyanates
Fouad, Moustafa H.,Ismailani, Uzair S.,Mair, Braeden A.,Munch, Maxime,Rotstein, Benjamin H.
supporting information, p. 2746 - 2750 (2020/04/16)
Amides were prepared using rhodium-catalyzed coupling of organozinc iodides and carbon-11 (11C, t1/2 = 20.4 min) isocyanates. Nonradioactive isocyanates and sp3 or sp2 organozinc iodides generated amides in yields of 13%-87%. Incorporation of cyclotron-produced [11C]CO2 into 11C-amide products proceeded in yields of 5%-99%. The synthetic utility of the methodology was demonstrated through the isolation of [11C]N-(4-fluorophenyl)-4-methoxybenzamide ([11C]6g) with a molar activity of 267 GBq μmol-1 and 12% radiochemical yield in 21 min from the beginning of synthesis.
Arylzinc Halides by Silver Catalyzed Zinc Insertion into Aryl Iodides
Casotti, Gianluca,Iuliano, Anna,Carpita, Adriano
, p. 1021 - 1026 (2019/01/04)
A catalytic amount of silver acetate efficiently promotes direct insertion of zinc metal into aryl iodides, having different structure, in ethereal solvent. Electron-rich substrates also rapidly undergo oxidative metalation. The arylzinc iodides formed give Negishi coupling products under mild reaction conditions to obtain biaryls in high yields. Sensitive functional groups like aldehydes and primary amides are well-tolerated.
Mechanochemical Activation of Zinc and Application to Negishi Cross-Coupling
Cao, Qun,Howard, Joseph L.,Wheatley, Emilie,Browne, Duncan L.
supporting information, p. 11339 - 11343 (2018/08/28)
A form independent activation of zinc, concomitant generation of organozinc species and engagement in a Negishi cross-coupling reaction via mechanochemical methods is reported. The reported method exhibits a broad substrate scope for both C(sp3)–C(sp2) and C(sp2)–C(sp2) couplings and is tolerant to many important functional groups. The method may offer broad reaching opportunities for the in situ generation organometallic compounds from base metals and their concomitant engagement in synthetic reactions via mechanochemical methods.
Ni-Catalyzed Regioselective Alkylarylation of Vinylarenes via C(sp3)-C(sp3)/C(sp3)-C(sp2) Bond Formation and Mechanistic Studies
Kc, Shekhar,Dhungana, Roshan K.,Shrestha, Bijay,Thapa, Surendra,Khanal, Namrata,Basnet, Prakash,Lebrun, Robert W.,Giri, Ramesh
supporting information, p. 9801 - 9805 (2018/08/06)
We report a Ni-catalyzed regioselective alkylarylation of vinylarenes with alkyl halides and arylzinc reagents to generate 1,1-diarylalkanes. The reaction proceeds well with primary, secondary and tertiary alkyl halides, and electronically diverse arylzinc reagents. Mechanistic investigations by radical probes, competition studies and quantitative kinetics reveal that the current reaction proceeds via a Ni(0)/Ni(I)/Ni(II) catalytic cycle by a rate-limiting direct halogen atom abstraction via single electron transfer to alkyl halides by a Ni(0)-catalyst.
Ni-Catalyzed Regioselective Dicarbofunctionalization of Unactivated Olefins by Tandem Cyclization/Cross-Coupling and Application to the Concise Synthesis of Lignan Natural Products
Kc, Shekhar,Basnet, Prakash,Thapa, Surendra,Shrestha, Bijay,Giri, Ramesh
, p. 2920 - 2936 (2018/03/09)
We disclose a (terpy)NiBr2-catalyzed reaction protocol that regioselectively difunctionalizes unactivated olefins with tethered alkyl halides and arylzinc reagents. The reaction shows an excellent functional group tolerance (such as ketones, es
Ultrasound-Promoted Synthesis of Arylzinc Compounds Using Zinc Powder and Their Application to Palladium(0)-Catalyzed Synthesis of Multifunctional Biaryls
Takagi, Kentaro
, p. 469 - 472 (2007/10/02)
Arylzinc compounds containing electron-withdrawing groups such as CO2CH3, CON(CH3)2, CN, Br, Cl, or CF3 at ortho position were prepared readily by the ultrasound-promoted reaction of aryl iodides with zinc powder, which were applied to palladium(0)-catalyzed cross-coupling with aryl halides to afford unsymmetrical and multifunctional biaryls in good yields.
