- Systematic Variation of Ligand and Cation Parameters Enables Site-Selective C-C and C-N Cross-Coupling of Multiply Chlorinated Arenes through Substrate-Ligand Electrostatic Interactions
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Use of attractive noncovalent interactions between ligand and substrate is an emerging strategy for controlling positional selectivity. A key question relates to whether fine control on molecules with multiple, closely spaced reactive positions is achievable using typically less directional electrostatic interactions. Herein, we apply a 10-piece "toolkit"comprising of two closely related sulfonated phosphine ligands and five bases, each possessing varying cation size, to the challenge of site-selective cross-coupling of multiply chlorinated arenes. The fine tuning provided by these ligand/base combinations is effective for Suzuki-Miyaura coupling and Buchwald-Hartwig coupling on a range of isomeric dichlorinated and trichlorinated arenes, substrates that would produce intractable mixtures when typical ligands are used. This study develops a practical solution for site-selective cross-coupling to generate complex, highly substituted arenes.
- Golding, William A.,Schmitt, Hendrik L.,Phipps, Robert J.
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supporting information
p. 21891 - 21898
(2021/01/11)
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- Isoquinoline compound melanocortin receptor ligands and methods of using same
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The invention relates to melanocortin receptor ligands and methods of using the ligands to alter or regulate the activity of a melanocortin receptor. The invention further relates to tetrahydroisoquinoline aromatic amines that function as melanocortin receptor ligands and as agents for controlling cytokine-regulated physiologic processes and pathologies, and combinatorial libraries thereof.
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- Electrophilic Amination Reagents: A New Method For The Preparation Of 3-Aryl-N-BOC (or N-FMOC) Oxaziridines
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N-BOC or N-FMOC benzaldimines are oxidized to the corresponding 3-Aryl-N-BOC or N-FMOC oxaziridines by reaction with Li m-chloroperoxybenzoate under aprotic conditions.The new oxaziridines can transfer their N-BOC or N-FMOC group to morpholine to give the corresponding Nβ-protected hydrazines.
- Vidal, Joelle,Damestoy, Stephanie,Collet, Andre
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p. 1439 - 1442
(2007/10/02)
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