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Literature DB >> 34706124

Visible Light Induced Brønsted Acid Assisted Pd-Catalyzed Alkyl Heck Reaction of Diazo Compounds and N-Tosylhydrazones.

Ziyan Zhang¹, Nikita Kvasovs¹, Anastasiia Dubrovina¹, Vladimir Gevorgyan¹.

Abstract

A mild visible light-induced palladium-catalyzed alkyl Heck reaction of diazo compounds and N-tosylhydrazones is reported. A broad range of vinyl arenes and heteroarenes with high functional group tolerance, as well as a range of different diazo compounds, can efficiently undergo this transformation. This method features Brønsted acid-assisted generation of hybrid palladium C(sp3 )-centered radical intermediate, which allowed for new selective C-H functionalization protocol.

Entities: Chemical

Keywords: Heck reaction; diazo compounds; palladium; radicals; reaction mechanisms

Year: 2021 PMID： 34706124 PMCID： PMC8712420 DOI： 10.1002/anie.202110924

Source DB: PubMed Journal: Angew Chem Int Ed Engl ISSN： 1433-7851 Impact factor: 15.336

49 in total

1. Thermal rearrangements of vinylcyclopropanes to cyclopentenes.

Authors: John E Baldwin
Journal: Chem Rev Date: 2003-04 Impact factor: 60.622

2. Heck Reaction of Electronically Diverse Tertiary Alkyl Halides.

Authors: Daria Kurandina; Mónica Rivas; Maxim Radzhabov; Vladimir Gevorgyan
Journal: Org Lett Date: 2018-01-05 Impact factor: 6.005

3. Aliphatic Radical Relay Heck Reaction at Unactivated C(sp³ )-H Sites of Alcohols.

Authors: Padon Chuentragool; Dongari Yadagiri; Taiki Morita; Sumon Sarkar; Marvin Parasram; Yang Wang; Vladimir Gevorgyan
Journal: Angew Chem Int Ed Engl Date: 2019-01-17 Impact factor: 15.336

4. Expanding Anti-Stokes Shifting in Triplet-Triplet Annihilation Upconversion for In Vivo Anticancer Prodrug Activation.

Authors: Ling Huang; Yang Zhao; He Zhang; Kai Huang; Jinyi Yang; Gang Han
Journal: Angew Chem Int Ed Engl Date: 2017-10-10 Impact factor: 15.336

10. Irradiation-Induced Palladium-Catalyzed Decarboxylative Heck Reaction of Aliphatic N-(Acyloxy)phthalimides at Room Temperature.

Authors: Guang-Zu Wang; Rui Shang; Yao Fu
Journal: Org Lett Date: 2018-01-18 Impact factor: 6.005

1 in total

Review 1. Photocatalytic C(sp³) radical generation via C-H, C-C, and C-X bond cleavage.

Authors: Chia-Yu Huang; Jianbin Li; Chao-Jun Li
Journal: Chem Sci Date: 2022-04-18 Impact factor: 9.969

1 in total

Visible Light Induced Brønsted Acid Assisted Pd-Catalyzed Alkyl Heck Reaction of Diazo Compounds and N-Tosylhydrazones.

1. Thermal rearrangements of vinylcyclopropanes to cyclopentenes.

2. Heck Reaction of Electronically Diverse Tertiary Alkyl Halides.

3. Aliphatic Radical Relay Heck Reaction at Unactivated C(sp³ )-H Sites of Alcohols.

4. Expanding Anti-Stokes Shifting in Triplet-Triplet Annihilation Upconversion for In Vivo Anticancer Prodrug Activation.

5. Transition-Metal-Catalyzed Cross-Couplings through Carbene Migratory Insertion.

6. Asymmetric Catalysis with Organic Azides and Diazo Compounds Initiated by Photoinduced Electron Transfer.

Review 7. Application of donor/acceptor-carbenoids to the synthesis of natural products.

Review 8. Catalytic C-H functionalization by metal carbenoid and nitrenoid insertion.

Review 9. Recent progress on donor and donor-donor carbenes.

10. Irradiation-Induced Palladium-Catalyzed Decarboxylative Heck Reaction of Aliphatic N-(Acyloxy)phthalimides at Room Temperature.

Review 1. Photocatalytic C(sp³) radical generation via C-H, C-C, and C-X bond cleavage.

Review 7. Application of donor/acceptor-carbenoids to the synthesis of natural products.

Review 8. Catalytic C-H functionalization by metal carbenoid and nitrenoid insertion.

Review 9. Recent progress on donor and donor-donor carbenes.

Review 1. Photocatalytic C(sp3) radical generation via C-H, C-C, and C-X bond cleavage.

Review 1. Photocatalytic C(sp³) radical generation via C-H, C-C, and C-X bond cleavage.