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Literature DB >> 23662848

Pd-catalyzed C-H lactonization for expedient synthesis of biaryl lactones and total synthesis of cannabinol.

Yan Li¹, Yan-Jun Ding, Jian-Yong Wang, Yi-Ming Su, Xi-Sheng Wang.

Abstract

A practical Pd(II)/Pd(IV)-catalyzed carboxyl-directed C-H activation/C-O cyclization to construct biaryl lactones has been developed. The synthetic utility of this new reaction was demonstrated in an atom-economical and operationally convenient total synthesis of the natural product cannabinol from commercially available starting materials, with the newly developed method used for two key steps.

Entities: Chemical

Mesh：

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Year: 2013 PMID： 23662848 DOI： 10.1021/ol400877q

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

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Cited

14 in total

1. Ligand-Accelerated ortho-C-H Olefination of Phenylacetic Acids.

Authors: Keary M Engle; Navid Dastbaravardeh; Peter S Thuy-Boun; Dong-Hui Wang; Aaron C Sather; Jin-Quan Yu
Journal: Organic Synth Date: 2015-03-12

2. A metal-free aromative cascade for the synthesis of diverse heterocycles.

Authors: Steven C Schlitzer; Dhanarajan Arunprasath; Katelyn G Stevens; Indrajeet Sharma
Journal: Org Chem Front Date: 2020-01-02 Impact factor: 5.281

3. General and practical carboxyl-group-directed remote C-H oxygenation reactions of arenes.

Authors: Yang Wang; Anton V Gulevich; Vladimir Gevorgyan
Journal: Chemistry Date: 2013-10-21 Impact factor: 5.236

4. Rh(iii)-catalyzed synthesis of dibenzo[b,d]pyran-6-ones from aryl ketone O-acetyl oximes and quinones via C-H activation and C-C bond cleavage.

Authors: Wei Yang; Haonan Zhang; Yu Liu; Cuiman Tang; Xiaohui Xu; Jiaqi Liu
Journal: RSC Adv Date: 2022-05-12 Impact factor: 4.036

5. Pd(II)-catalyzed C-H functionalizations directed by distal weakly coordinating functional groups.

Authors: Gang Li; Li Wan; Guofu Zhang; Dasheng Leow; Jillian Spangler; Jin-Quan Yu
Journal: J Am Chem Soc Date: 2015-03-24 Impact factor: 15.419

6. From Pd(OAc)₂ to Chiral Catalysts: The Discovery and Development of Bifunctional Mono-N-Protected Amino Acid Ligands for Diverse C-H Functionalization Reactions.

Authors: Qian Shao; Kevin Wu; Zhe Zhuang; Shaoqun Qian; Jin-Quan Yu
Journal: Acc Chem Res Date: 2020-03-31 Impact factor: 22.384

Pd-catalyzed C-H lactonization for expedient synthesis of biaryl lactones and total synthesis of cannabinol.

1. Ligand-Accelerated ortho-C-H Olefination of Phenylacetic Acids.

2. A metal-free aromative cascade for the synthesis of diverse heterocycles.

3. General and practical carboxyl-group-directed remote C-H oxygenation reactions of arenes.

4. Rh(iii)-catalyzed synthesis of dibenzo[b,d]pyran-6-ones from aryl ketone O-acetyl oximes and quinones via C-H activation and C-C bond cleavage.

5. Pd(II)-catalyzed C-H functionalizations directed by distal weakly coordinating functional groups.

6. From Pd(OAc)₂ to Chiral Catalysts: The Discovery and Development of Bifunctional Mono-N-Protected Amino Acid Ligands for Diverse C-H Functionalization Reactions.

Review 7. Electrochemistry and Photoredox Catalysis: A Comparative Evaluation in Organic Synthesis.

8. Relative Strength of Common Directing Groups in Palladium-Catalyzed Aromatic C-H Activation.

9. Applications of C-H functionalization logic to cyclobutane synthesis.

10. Synthesis of ethoxy dibenzooxaphosphorin oxides through palladium-catalyzed C(sp(2))-H activation/C-O formation.