Reductive Lithiation in the Absence of Aromatic Electron Carriers. A Steric Effect Manifested on the Surface of Lithium Metal Leads to a Difference in Relative Reactivity Depending on Whether the Aromatic Electron Carrier Is Present or Absent-Reference-Cited by-同舟云学术

Reductive Lithiation in the Absence of Aromatic Electron Carriers. A Steric Effect Manifested on the Surface of Lithium Metal Leads to a Difference in Relative Reactivity Depending on Whether the Aromatic Electron Carrier Is Present or Absent

Published:2015-08-14 Issue:17 Volume:80 Page:8571-8582
ISSN:0022-3263
Container-title:The Journal of Organic Chemistry
language:en
Short-container-title:J. Org. Chem.

Author:

Kennedy Nicole¹,Lu Gang¹,Liu Peng¹,Cohen Theodore¹

Affiliation:

1. Department of Chemistry, University of Pittsburgh, Pittsburgh, Pennsylvania 15260, United States

Publisher

American Chemical Society (ACS)

Subject

Organic Chemistry

Link

https://pubs.acs.org/doi/pdf/10.1021/acs.joc.5b01136

Reference91 articles.

1. Hydrolithiation of .alpha.-olefins by a regiospecific two-step process. Transformation of alkyl phenyl sulfides to alkyllithium reagents

2. Markownikoff two-step hydrolithiation of .alpha.-olefins. Transformation of secondary and tertiary alkyl phenyl sulfides to the relevant alkyllithium reagents

3. A simple preparation of sulfur-stabilized cyclopropyl anions via reductive lithiation of cyclopropanone dithioketals.

4. The conversion of carboxylic acids and esters into acyl anion equivalents via reduction lithiation of their ketene phenylthioacetal derivatives

5. Organoalkali compounds by radical anion induced reductive metalation of phenyl thioethers

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