AI Article Synopsis

  • - The text describes a chemical process where Grignard reagents are added to specific compounds (2-halocyclohex-2-en-1-ones) to create meta-substituted phenols, with the new substituent coming from the Grignard reagent.
  • - Various types of organometallic reagents can be used, including those with alkyl, allyl, alkynyl, aryl, and heteroaryl groups, even if they contain fluorine.
  • - Prior to the Grignard addition, the initial compound can be modified by reacting it with carbon, fluorine, or sulfur electrophiles after deprotonation, leading to the formation of highly substituted phenols.

Article Abstract

Addition of Grignard or other organometallic reagents to 2-halocyclohex-2-en-1-ones bearing an alkyl or aryl group at C-5, followed by mild acid treatment and exposure to 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) at room temperature, generates meta-substituted phenols in which the newly introduced meta substituent originates from the Grignard reagent. The range of effective organometallic reagents includes alkyl, allyl, alkynyl, aryl, and heteroaryl compounds including those with fluorine substituents. The initial halocyclohexenone can be deprotonated at C-6 and reacted with carbon, fluorine, or sulfur electrophiles before the Grignard addition so as to generate highly substituted phenols.

Download full-text PDF

Source
http://dx.doi.org/10.1021/acs.joc.6b01653DOI Listing

Publication Analysis

Top Keywords

meta-substituted phenols
8
organometallic reagents
8
formation meta-substituted
4
phenols transition
4
transition metal-free
4
metal-free aromatization
4
aromatization 2-bromocyclohex-2-en-1-ones
4
2-bromocyclohex-2-en-1-ones addition
4
addition grignard
4
grignard organometallic
4

Similar Publications

Want AI Summaries of new PubMed Abstracts delivered to your In-box?

Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!