Selective cleavage of C-H bond to achieve regio- and enantioselective C-H functionalization is always the top mission of study of C-H activation. By combining weakly coordinating directing group and newly designed ligands we could achieve selective meta-C(sp2)–H functionalization of amide and enantioselective C(sp3)–H functionalization of free carboxylic acid. 2-carbomethoxynorbornene is identified as a more effective transient mediator to promote a Pd(II)-catalyzed meta-C(sp2)–H alkylation of amides with various alkyl iodides as well as arylation with previously incompatible aryl iodides. The use of a tailor-made quinoline ligand is also crucial for this reaction to proceed. On the other hand, a new type of bidentate chiral oxazoline ligand has been developed and demonstrated to achieve enantioselective C(sp3)–H arylation on carboxylic acid derivative. With this new ligand, we could achieve the enantioselective C(sp3)–H arylation, alkenylation and alkynylation of isobutyramide as well as 2-aminoisobutyramide.

Achieving regio- and enantioselective Pd-catalyzed C-H functionalization through new ligand design

256th National Meeting (2018)

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