E-resources
Peer reviewed
-
Song, Lei; Fu, Dong‐Min; Chen, Liang; Jiang, Yuan‐Xu; Ye, Jian‐Heng; Zhu, Lei; Lan, Yu; Fu, Qiang; Yu, Da‐Gang
Angewandte Chemie International Edition, November 16, 2020, Volume: 59, Issue: 47Journal Article
Remote difunctionalization of unactivated alkenes is challenging but a highly attractive tactic to install two functional groups across long distances. Reported herein is the first remote difunctionalization of alkenes with CO2. This visible‐light photoredox catalysis strategy provides a facile method to synthesize a series of carboxylic acids bearing valuable fluorine‐ or phosphorus‐containing functional groups. Moreover, this versatile protocol shows mild reaction conditions, broad substrate scope, and good functional‐group tolerance. Based on DFT calculations, a radical adds to an unactivated alkene to smoothly form a new carbon radical, followed by a 1,5‐hydrogen atom‐transfer process, the rate‐limiting step, generating a more stable benzylic radical. The reduction of the benzylic radicals by an IrII species generates the corresponding benzylic carbanions as the key intermediates, which further undergo nucleophilic attack with CO2 to generate carboxylates. Reported is the first remote difunctionalization of unactivated alkenes with CO2 by visible‐light photoredox catalysis. Mechanistic studies indicate that a 1,5‐hydrogen atom‐transfer process is the rate‐limiting step and reduction of radical intermediates generates the corresponding carbanions. Other electrophiles, including aldehydes, ketones, and benzylic bromides, are also applicable in this process, demonstrating a general strategy for redox‐neutral remote difunctionalization of unactivated alkenes.
Author
Shelf entry
Permalink
- URL:
Impact factor
Access to the JCR database is permitted only to users from Slovenia. Your current IP address is not on the list of IP addresses with access permission, and authentication with the relevant AAI accout is required.
Year | Impact factor | Edition | Category | Classification | ||||
---|---|---|---|---|---|---|---|---|
JCR | SNIP | JCR | SNIP | JCR | SNIP | JCR | SNIP |
Select the library membership card:
If the library membership card is not in the list,
add a new one.
DRS, in which the journal is indexed
Database name | Field | Year |
---|
Links to authors' personal bibliographies | Links to information on researchers in the SICRIS system |
---|
Source: Personal bibliographies
and: SICRIS
The material is available in full text. If you wish to order the material anyway, click the Continue button.