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Diols are compounds with two hydroxyl groups. In addition to syn dihydroxylation, diols can also be synthesized through the process of anti dihydroxylation. The process involves treating an alkene with a peroxycarboxylic acid to form an epoxide. Epoxides are highly strained three-membered rings with oxygen and two carbons occupying the corners of an equilateral triangle. This step is followed by ring-opening of the epoxide in the presence of an aqueous acid to give a trans diol.
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Ziegler–Natta polymerization is another form of addition or chain‐growth polymerization used for synthesizing linear polymers over branched polymers. The catalyst used for polymerization is the Ziegler–Natta catalyst, named after Karl Ziegler and Giulio Natta, who developed it in 1953. This catalyst is an organometallic complex of titanium tetrachloride and triethyl aluminum, with the active form of the catalyst being an alkyl titanium compound. Using the Ziegler–Natta...
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Nucleophilic Addition to the Carbonyl Group: General Mechanism01:18

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Cycloadditions are one of the most valuable and effective synthesis routes to form cyclic compounds. These are concerted pericyclic reactions between two unsaturated compounds resulting in a cyclic product with two new σ bonds formed at the expense of π bonds. The [4 + 2] cycloaddition, known as the Diels–Alder reaction, is the most common. The other example is a [2 + 2] cycloaddition.
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Radicals can be formed by adding a radical to a spin-paired molecule. This is typically observed with unsaturated species, where the addition of a radical across the π bond leads to the production of a new radical by dissolving the π bond. For example, the addition of a Br radical to an alkene yields a carbon-centered radical.
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The reaction of hydrogen bromide with alkenes in the presence of hydroperoxides or peroxides proceeds via anti-Markovnikov addition. The radical chain reaction comprises initiation, propagation, and termination steps.
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Late-Stage C(sp2)-C(sp3) Diversification via Nickel Oxidative Addition Complexes.

Carlota Odena1,2, Tomás G Santiago1, María Lourdes Linares3

  • 1Institute of Chemical Research of Catalonia (ICIQ), The Barcelona Institute of Science and Technology, Avenida Països Catalans 16, 43007 Tarragona, Spain.

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|July 25, 2024
PubMed
Summary
This summary is machine-generated.

Nickel oxidative addition complexes (Ni-OACs) offer a new platform for drug discovery. This approach rapidly generates lead candidates with enhanced C(sp3) fraction, accelerating the design-make-test-analyze cycle.

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Area of Science:

  • Organic Chemistry
  • Medicinal Chemistry
  • Catalysis

Background:

  • Drug discovery often faces challenges in accessing novel chemical space, particularly with high C(sp3) fractions.
  • Traditional nickel-catalyzed reactions can be limited in scope and require specialized ligands.

Purpose of the Study:

  • To introduce nickel oxidative addition complexes (Ni-OACs) as a versatile platform for rapid lead candidate generation.
  • To explore the potential of Ni-OACs in accessing new chemical space beyond C(sp2)-C(sp3) couplings.
  • To demonstrate an automated diversification process for expediting drug discovery.

Main Methods:

  • Synthesis and characterization of Ni-OACs derived from drug-like molecules.
  • Evaluation of Ni-OACs in various bond-forming reactions, including C(sp2)-C(sp3) couplings.
  • Development and implementation of an automated diversification workflow.

Main Results:

  • Ni-OACs enable rapid generation of lead candidates with enhanced C(sp3) fraction.
  • Ni-OACs demonstrate broad applicability in diverse bond formations, surpassing conventional Ni-catalyzed methods.
  • The automated diversification process highlights the robustness and efficiency of the Ni-OAC platform.

Conclusions:

  • Ni-OACs provide a powerful and generalizable strategy for accessing novel chemical entities.
  • This platform significantly accelerates the design-make-test-analyze (DMTA) cycle in drug discovery.
  • Ni-OACs represent a promising new gateway for medicinal chemistry and lead optimization.