Amidocuprates for Directed ortho Cupration: Structural Study, Mechanistic Investigation, and Chemical Requirements

The name of the game: X‐ray crystallographic analysis of Gilman‐ and Lipshutz‐type amidocuprates indicates that the presence of LiX (X=CN, I) and THF shifts the equilibrium between the two toward the Lipshutz‐type cuprate and that this is important in generating the active species for directed ortho...

Full description

Saved in:
Bibliographic Details
Published in:Angewandte Chemie (International ed.) 2012-11, Vol.51 (48), p.12081-12085
Main Authors: Komagawa, Shinsuke, Usui, Shinya, Haywood, Joanna, Harford, Philip J., Wheatley, Andrew E. H., Matsumoto, Yotaro, Hirano, Keiichi, Takita, Ryo, Uchiyama, Masanobu
Format: Article
Language:English
Subjects:
Amides - chemistry
Copper - chemistry
COPPER OXIDE
Crystallography
Crystallography, X-Ray
Cuprates
density functional calculations
MATHEMATICAL ANALYSIS
mechanistic studies
MICA
Molecular Structure
Names
Organometallic Compounds - chemistry
ortho metalation
Stereoisomerism
structure elucidation
X RAYS
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:The name of the game: X‐ray crystallographic analysis of Gilman‐ and Lipshutz‐type amidocuprates indicates that the presence of LiX (X=CN, I) and THF shifts the equilibrium between the two toward the Lipshutz‐type cuprate and that this is important in generating the active species for directed ortho cupration. DFT calculations show that monomeric Gilman‐type cuprates have an unprecedentedly high reactivity (see scheme, DG=directing group).
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201204923