Convenient and flexible syntheses of gem-dimethyl carboxylic triggers via mono-selective β-C(sp3)–H arylation of pivalic acid with ortho-substituted aryl iodides. Issue 12 (10th May 2022)

• Record Type: Journal Article
• Authors: Huang, Yongliang; Du, Yu; Su, Weiping
• Is Part Of: Organic chemistry frontiers. Volume 9:Issue 12(2022)
• Page Start: 3293
• Page End: 3300
• Publication Date: 2022-05-10
• Subjects: Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1039/d2qo00478j
• Languages: English
• ISSNs: 2052-4110

Abstract

Abstract : A Pd(ii )-catalyzed C(sp 3 )–H mono-arylation of pivalic acid is presented, implementing the convenient and flexible synthesis of trimethyl-lock-type triggers – 3-aryl-2, 2-dimethylpropanoic acids bearing ortho -activatable substituents. Abstract : This work presents a palladium(ii )-catalyzed mono-selective C(sp 3 )–H arylation of pivalic acid for rapid construction of an important library of 3-aryl-2, 2-dimethylpropanoic acids, especially ortho -substituted-aryl compounds. The strategy greatly streamlines access to a series of trimethyl-lock-type triggers – arylated gem -dimethyl carboxylic acids bearing ortho -activatable substituents, which can be used as a self-immolative spacer for selective chemical release initiated under specific conditions. Flexible transformation and derivatization of these activatable carboxylic triggers are also showcased.