Nicholas D. Chiappini

ORCID: 0000-0003-0469-1008
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About
Contact & Profiles
Research Areas
  • Catalytic C–H Functionalization Methods
  • Synthesis and Catalytic Reactions
  • Sulfur-Based Synthesis Techniques
  • Synthesis of β-Lactam Compounds
  • Phenothiazines and Benzothiazines Synthesis and Activities
  • Oxidative Organic Chemistry Reactions
  • Radical Photochemical Reactions
  • Cyclopropane Reaction Mechanisms
  • Asymmetric Hydrogenation and Catalysis
  • Synthetic Organic Chemistry Methods
  • Crystallization and Solubility Studies
  • Chemical Synthesis and Analysis
  • Catalytic Cross-Coupling Reactions
  • Microbial Natural Products and Biosynthesis
  • X-ray Diffraction in Crystallography

Princeton University
2021-2024

University of North Carolina Wilmington
2024

Stanford University
2018-2019

Drew University
2013

A general and operationally convenient method for intermolecular amination of C(sp3 )-H bonds is described. This technology allows efficient functionalization complex molecules, including numerous pharmaceutical targets. The combination pivalonitrile as a solvent, Al2 O3 an additive, phenyl sulfamate nitrogen source affords differential reaction performance substrate scope. Mechanistic data strongly implicate pathway catalyst decomposition that initiates with solvent oxidation, thus...

10.1002/anie.201713225 article EN Angewandte Chemie International Edition 2018-02-27

A light-driven method for the generation of aryl radicals from triarylbismuth(III) and (V) reagents is described. Aryl radical proposed to occur through ligand-assisted mesolytic cleavage an organobismuth(IV) intermediate generated either oxidation BiIII or reduction BiV. This mode demonstrated be compatible with a range bimolecular arylations, including hydroarylation electron-deficient olefins arylation diboronates, disulfides, sulfonyl cyanides, phosphites, isocyanides. The intermediacy...

10.1021/acscatal.3c05598 article EN ACS Catalysis 2024-02-06

Abstract A general and operationally convenient method for intermolecular amination of C(sp 3 )−H bonds is described. This technology allows efficient functionalization complex molecules, including numerous pharmaceutical targets. The combination pivalonitrile as a solvent, Al 2 O an additive, phenyl sulfamate nitrogen source affords differential reaction performance substrate scope. Mechanistic data strongly implicate pathway catalyst decomposition that initiates with solvent oxidation,...

10.1002/ange.201713225 article EN Angewandte Chemie 2018-02-27

The preparation of substituted azetidines and larger ring, nitrogen-containing saturated heterocycles is enabled through efficient selective intermolecular sp3-C–H amination alkyl bromide derivatives. A range substrates are demonstrated to undergo C–H subsequent sulfamate alkylation in good excellent yield. N-Phenoxysulfonyl-protected products can be unmasked under neutral or mild basic conditions yield the corresponding cyclic secondary amines. preparative convenience this protocol...

10.1021/acs.orglett.9b04096 article EN Organic Letters 2019-12-24

The desire for maximally efficient transformations in complex molecule synthesis has contributed to a surge of interest C–H functionalization methods development recent years. In contrast the steady stream methodological reports, however, there are noticeably fewer studies comparing efficacies different protocols on single structurally intricate substrate. Recognizing importance heteroatom incorporation synthesis, this report discloses comparative examination diverse strategies C–O, C–N, and...

10.1021/acs.joc.7b03291 article EN publisher-specific-oa The Journal of Organic Chemistry 2018-01-09

The preparation of substituted azetidines and larger-ring, nitrogen-containing saturated heterocycles is enabled through efficient selective intermolecular sp<sup>3</sup>-C–H amination alkyl bromide derivatives. A range substrates demonstrated to undergo C–H subsequent sulfamate alkylation in good excellent yield. <i>N</i>-Phenoxysulfonyl-protected products can be unmasked under neutral or mild basic conditions yield the corresponding cyclic 2° amines. preparative...

10.26434/chemrxiv.9734000 preprint EN cc-by-nc-nd 2019-08-28

The preparation of substituted azetidines and larger-ring, nitrogen-containing saturated heterocycles is enabled through efficient selective intermolecular sp 3 -C–H amination alkyl bromide derivatives. A range substrates demonstrated to undergo C–H subsequent sulfamate alkylation in good excellent yield. N -Phenoxysulfonyl-protected products can be unmasked under neutral or mild basic conditions yield the corresponding cyclic 2° amines. preparative convenience this protocol gram-scale...

10.26434/chemrxiv.9734000.v1 preprint EN cc-by-nc-nd 2019-08-28
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