Copper(I)-Promoted C–N Cross-Coupling of N-Heterocyclic Compounds with 1,2-Di(pyrimidin-2-yl) Disulfides

The Pd-catalyzed, Cu I Àcarboxylate-mediated crosscoupling reactiono fo rganosulfur compounds with nucleophilic organometallic reagents is knowna st he Liebeskind-Srogl cross-coupling reaction. Owing to the readily available starting materials and neutral reactionc onditions, it has become an attractive procedure for the formation of carbonÀcarbon bonds, in particularf or cases in whicht radi-tional methods had failed. Since the seminal work of Liebeskind and Srogl in 2000, this reactionh as received intense attentionf rom the synthetic community.I nt his Focus Review,w eh ighlight recent advances in this intriguing cross-coupling reactiona nd its applications in organic synthesis.Scheme1.Liebeskind-Srogl cross-coupling reaction.Scheme2.The original Liebeskind-Sroglc ross-coupling reaction.d ba = dibenzylideneacetone, TFP = tri-2-furanylphosphine [a] Dr.Scheme4.Cross-coupling reaction between a-amino acid thiol esters and organostannanes. Cbz = benzyloxycarbonyl.Scheme5.Cross-coupling reaction between thiol esters and B-alkyl-9-BBN. 9-BBN = 9-borabicyclo[3.3.1]nonane.Scheme6.One-pothydroboration/intramolecular-cross-couplingr eaction between thiol esters and B-alkyl-9-BBN. DIPEA = N,N-diisopropylethylamine.Scheme7.Cross-coupling reaction between thiol esters andorganoindium reagents.Scheme8.Cross-coupling reaction between thiol esters andorganosilicon reagents. TBAF = tetra-n-butylammonium fluoride.Scheme9.Intramolecular cross-coupling reaction between thiol esters and olefins.Scheme38. Cross-coupling reaction between diaryld isulfides and boronicacids/terminal-alkynes.Scheme55. Synthesis of the C 15 ÀC 36 segment of goniodomin A. TBS = tert-butyldimethylsilyl, TBDPS = tert-butyldiphenylsilyl.Scheme56. To talsynthesis of verbenachalcone. MOM = methoxymethyl.Scheme57. Synthesis of enigmol and its stereoisomers. Boc = tert-butyloxycarbonyl.Scheme58. To talsynthesis of (À)-agelastatins A-F.Scheme59. Synthesis of quinone-containing salvinorin Aa nalogues.Scheme60. Synthesis of Soai-type aldehydes.

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The Liebeskind–Srogl Cross‐Coupling Reaction and its Synthetic Applications

Cheng

Chen

Liu

et al. 2018

Asian J Org Chem

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The palladium‐catalyzed C‐N cross‐coupling reaction of diheteroaryl disulfides with heterocyclic amines

Liu

Zhang

Quan

et al. 2017

Applied Organom Chemis

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The Pd‐catalyzed cross‐coupling reaction of 1, 2‐di(pyrimidin‐2‐yl) disulfides with heterocyclic amines including 2‐amino pyrimidines and 1,3,4‐thiadiazol‐2‐amines to deliver symmetrical C‐N coupling products in moderate to good yields is reported. This method provides an opportunity for synthesis of bioactive molecules and pharmaceutically interesting compounds containing heterocycle motifs. The reported protocol shows good functional group compatibility, and provides a new strategy for preparation of C2‐amination pyrimidine derivatives from heterocyclic disulfides.

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ChemInform Abstract: Copper(I)‐Promoted C—N Cross‐Coupling of N‐Heterocyclic Compounds with 1,2‐Di(pyrimidin‐2‐yl) Disulfides.

et al. 2016

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Copper(I)-Promoted C–N Cross-Coupling of N-Heterocyclic Compounds with 1,2-Di(pyrimidin-2-yl) Disulfides

Abstract: A CuTC-promoted C-N cross-coupling of 1,2-di(pyrimidin-2yl) disulfides with N-heterocyclic compounds including indoles, triazole benzotriazole, and benzoimidazole by C-S cleavage of the disulfides is reported.

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The Liebeskind–Srogl Cross‐Coupling Reaction and its Synthetic Applications

The Liebeskind–Srogl Cross‐Coupling Reaction and its Synthetic Applications

The palladium‐catalyzed C‐N cross‐coupling reaction of diheteroaryl disulfides with heterocyclic amines

ChemInform Abstract: Copper(I)‐Promoted C—N Cross‐Coupling of N‐Heterocyclic Compounds with 1,2‐Di(pyrimidin‐2‐yl) Disulfides.

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