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Literature DB >> 26034336

Computational predictions of substituted benzyne and indolyne regioselectivities.

Abstract

A computational study using DFT methods was performed for an array of mono and disubstituted benzynes and indolynes. The inherent distortion present in the geometry-optimized structures predicts the regioselectivity of aryne trapping by nucleophiles or cycloaddition partners. These studies will serve to enable the further use of unsymmetrical arynes in organic synthesis.

Entities: Chemical Gene

Keywords: arynes; computations; hetarynes; heterocycles; regioselectivities

Year: 2015 PMID： 26034336 PMCID： PMC4448725 DOI： 10.1016/j.tetlet.2015.01.022

Source DB: PubMed Journal: Tetrahedron Lett ISSN： 0040-4039 Impact factor: 2.415

48 in total

1. Total synthesis of (-)-N-methylwelwitindolinone C isothiocyanate.

Authors: Alexander D Huters; Kyle W Quasdorf; Evan D Styduhar; Neil K Garg
Journal: J Am Chem Soc Date: 2011-08-11 Impact factor: 15.419

2. Arynes and cyclohexyne in natural product synthesis.

Authors: Christian M Gampe; Erick M Carreira
Journal: Angew Chem Int Ed Engl Date: 2012-03-15 Impact factor: 15.336

3. Synthesis and reactivity comparisons of 1-methyl-3-substituted cyclopropene mini-tags for tetrazine bioorthogonal reactions.

Authors: Jun Yang; Yong Liang; Jolita Šečkutė; K N Houk; Neal K Devaraj
Journal: Chemistry Date: 2014-02-24 Impact factor: 5.236

4. Aromaticity and activation strain analysis of [3 + 2] cycloaddition reactions between group 14 heteroallenes and triple bonds.

Authors: Israel Fernández; Fernando P Cossío; F Matthias Bickelhaupt
Journal: J Org Chem Date: 2011-03-09 Impact factor: 4.354

5. Cycloaddition reactions of butadiene and 1,3-dipoles to curved arenes, fullerenes, and nanotubes: theoretical evaluation of the role of distortion energies on activation barriers.

Authors: Sílvia Osuna; Kendall N Houk
Journal: Chemistry Date: 2009-12-07 Impact factor: 5.236

Computational predictions of substituted benzyne and indolyne regioselectivities.

1. Total synthesis of (-)-N-methylwelwitindolinone C isothiocyanate.

2. Arynes and cyclohexyne in natural product synthesis.

3. Synthesis and reactivity comparisons of 1-methyl-3-substituted cyclopropene mini-tags for tetrazine bioorthogonal reactions.

4. Aromaticity and activation strain analysis of [3 + 2] cycloaddition reactions between group 14 heteroallenes and triple bonds.

5. Cycloaddition reactions of butadiene and 1,3-dipoles to curved arenes, fullerenes, and nanotubes: theoretical evaluation of the role of distortion energies on activation barriers.

6. Extraordinary Difference in Reactivity of Ozone (OOO) and Sulfur Dioxide (OSO): A Theoretical Study.

7. Total synthesis of (-)-N-methylwelwitindolinone B isothiocyanate via a chlorinative oxabicycle ring-opening strategy.

8. Regioselective reactions of 3,4-pyridynes enabled by the aryne distortion model.

9. Concise enantiospecific total synthesis of tubingensin A.

10. Cycloadditions of cyclohexynes and cyclopentyne.

1. Expanding the ROMP Toolbox: Synthesis of Air-Stable Benzonorbornadiene Polymers by Aryne Chemistry.

2. Expanding the Strained Alkyne Toolbox: Generation and Utility of Oxygen-Containing Strained Alkynes.

3. Synthesis of Uracil-Iodonium(III) Salts for Practical Utilization as Nucleobase Synthetic Modules.

4. One-step synthesis of benzo[b]thiophenes by aryne reaction with alkynyl sulfides.

5. The Aryne Phosphate Reaction.

6. Concerted nucleophilic aromatic substitution with (19)F(-) and (18)F(-).

Review 7. Predictive and mechanistic multivariate linear regression models for reaction development.

Review 8. Uncovering the Neglected Similarities of Arynes and Donor-Acceptor Cyclopropanes.