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Literature DB >> 26635188

β-C(sp(3))-H Arylation of α-Hydroxy Acid Derivatives Utilizing Amino Acid as a Directing Group.

Tetsuya Toba¹, Yi Hu¹, Anh T Tran¹, Jin-Quan Yu¹.

Abstract

The Pd(II)-catalyzed arylation of unactivated β-C(sp(3))-H bonds in α-hydroxy aliphatic acid with a variety of aryl iodides was developed utilizing an amino acid auxiliary as a directing group. This protocol provides access to biologically active β-arylated-α-hydroxy acid derivatives.

Entities: Chemical Disease Species

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Year: 2015 PMID： 26635188 PMCID： PMC4817547 DOI： 10.1021/acs.orglett.5b02900

Source DB: PubMed Journal: Org Lett ISSN： 1523-7052 Impact factor: 6.005

23 in total

1. Key mechanistic features of enantioselective C-H bond activation reactions catalyzed by [(chiral mono-N-protected amino acid)-Pd(II)] complexes.

Authors: Djamaladdin G Musaev; Alexey Kaledin; Bing-Feng Shi; Jin-Quan Yu
Journal: J Am Chem Soc Date: 2012-01-09 Impact factor: 15.419

2. Auxiliary-assisted palladium-catalyzed arylation and alkylation of sp2 and sp3 carbon-hydrogen bonds.

Authors: Dmitry Shabashov; Olafs Daugulis
Journal: J Am Chem Soc Date: 2010-03-24 Impact factor: 15.419

3. Palladium-catalyzed asymmetric iodination of unactivated C-H bonds under mild conditions.

Authors: Ramesh Giri; Xiao Chen; Jin-Quan Yu
Journal: Angew Chem Int Ed Engl Date: 2005-03-29 Impact factor: 15.336

4. Ligand-accelerated ortho-C-H alkylation of arylcarboxylic acids using alkyl boron reagents.

Authors: Peter S Thuy-Boun; Giorgio Villa; Devin Dang; Paul Richardson; Shun Su; Jin-Quan Yu
Journal: J Am Chem Soc Date: 2013-11-08 Impact factor: 15.419

5. Ligand-accelerated C-H activation reactions: evidence for a switch of mechanism.

Authors: Keary M Engle; Dong-Hui Wang; Jin-Quan Yu
Journal: J Am Chem Soc Date: 2010-10-13 Impact factor: 15.419

6. Catalytic direct arylation with aryl chlorides, bromides, and iodides: intramolecular studies leading to new intermolecular reactions.

Authors: Louis-Charles Campeau; Mathieu Parisien; Annie Jean; Keith Fagnou
Journal: J Am Chem Soc Date: 2006-01-18 Impact factor: 15.419

4. Ni(ii)-catalyzed mono-selective ortho-arylation of unactivated aryl C-H bonds utilizing amino acids as a directing group.

Authors: Zhanqing Cong; Feng Gao; Hong Liu
Journal: RSC Adv Date: 2019-04-08 Impact factor: 4.036

4 in total

β-C(sp(3))-H Arylation of α-Hydroxy Acid Derivatives Utilizing Amino Acid as a Directing Group.

1. Key mechanistic features of enantioselective C-H bond activation reactions catalyzed by [(chiral mono-N-protected amino acid)-Pd(II)] complexes.

2. Auxiliary-assisted palladium-catalyzed arylation and alkylation of sp2 and sp3 carbon-hydrogen bonds.

3. Palladium-catalyzed asymmetric iodination of unactivated C-H bonds under mild conditions.

4. Ligand-accelerated ortho-C-H alkylation of arylcarboxylic acids using alkyl boron reagents.

5. Ligand-accelerated C-H activation reactions: evidence for a switch of mechanism.

6. Catalytic direct arylation with aryl chlorides, bromides, and iodides: intramolecular studies leading to new intermolecular reactions.

7. Mechanistic rationalization of unusual kinetics in Pd-catalyzed C-H olefination.

8. Palladium-catalyzed β-arylation of silyl ketene acetals and application to the synthesis of benzo-fused δ-lactones.

9. Conformation-induced remote meta-C-H activation of amines.

10. Ligand-promoted alkylation of C(sp3)-H and C(sp2)-H bonds.

1. Palladium-Catalyzed Transformations of Alkyl C-H Bonds.

Review 2. Transition-Metal-Catalyzed, Coordination-Assisted Functionalization of Nonactivated C(sp³)-H Bonds.

3. Pd-catalysed ligand-enabled carboxylate-directed highly regioselective arylation of aliphatic acids.

4. Ni(ii)-catalyzed mono-selective ortho-arylation of unactivated aryl C-H bonds utilizing amino acids as a directing group.

Review 2. Transition-Metal-Catalyzed, Coordination-Assisted Functionalization of Nonactivated C(sp3)-H Bonds.

Review 2. Transition-Metal-Catalyzed, Coordination-Assisted Functionalization of Nonactivated C(sp³)-H Bonds.