Irradiation-Induced Heck Reaction of Unactivated Alkyl Halides at Room Temperature
The palladium-catalyzed Mizoroki–Heck reaction is arguably one of the most significant carbon–carbon bond-construction reactions to be discovered in the last 50 years, with a tremendous number of applications in the production of chemicals. This Nobel-Prize-winning transformation has yet to overcome...
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| Published in | Journal of the American Chemical Society Vol. 139; no. 50; pp. 18307 - 18312 |
|---|---|
| Main Authors | , , , |
| Format | Journal Article |
| Language | English |
| Published |
WASHINGTON
American Chemical Society
20.12.2017
Amer Chemical Soc |
| Subjects | |
| Online Access | Get full text |
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| Abstract | The palladium-catalyzed Mizoroki–Heck reaction is arguably one of the most significant carbon–carbon bond-construction reactions to be discovered in the last 50 years, with a tremendous number of applications in the production of chemicals. This Nobel-Prize-winning transformation has yet to overcome the obstacle of its general application in a range of alkyl electrophiles, especially tertiary alkyl halides that possess eliminable β-hydrogen atoms. Whereas most palladium-catalyzed cross-coupling reactions utilize the ground-state reactivity of palladium complexes under thermal conditions and generally apply a single ligand system, we report that the palladium-catalyzed Heck reaction proceeds smoothly at room temperature with a variety of tertiary, secondary, and primary alkyl bromides upon irradiation with blue light-emitting diodes in the presence of a dual phosphine ligand system. We rationalize that this unprecedented transformation is achieved by utilizing the photoexcited-state reactivity of the palladium complex to enhance oxidative addition and suppress undesired β-hydride elimination. |
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| AbstractList | The palladium-catalyzed Mizoroki–Heck reaction is arguably one of the most significant carbon–carbon bond-construction reactions to be discovered in the last 50 years, with a tremendous number of applications in the production of chemicals. This Nobel-Prize-winning transformation has yet to overcome the obstacle of its general application in a range of alkyl electrophiles, especially tertiary alkyl halides that possess eliminable β-hydrogen atoms. Whereas most palladium-catalyzed cross-coupling reactions utilize the ground-state reactivity of palladium complexes under thermal conditions and generally apply a single ligand system, we report that the palladium-catalyzed Heck reaction proceeds smoothly at room temperature with a variety of tertiary, secondary, and primary alkyl bromides upon irradiation with blue light-emitting diodes in the presence of a dual phosphine ligand system. We rationalize that this unprecedented transformation is achieved by utilizing the photoexcited-state reactivity of the palladium complex to enhance oxidative addition and suppress undesired β-hydride elimination. The palladium-catalyzed Mizoroki-Heck reaction is arguably one of the most significant carbon-carbon bond-construction reactions to be discovered in the last 50 years, with a tremendous number of applications in the production of chemicals. This Nobel-Prize-winning transformation has yet to overcome the obstacle of its general application in a range of alkyl electrophiles, especially tertiary alkyl halides that possess eliminable β-hydrogen atoms. Whereas most palladium-catalyzed cross-coupling reactions utilize the ground-state reactivity of palladium complexes under thermal conditions and generally apply a single ligand system, we report that the palladium-catalyzed Heck reaction proceeds smoothly at room temperature with a variety of tertiary, secondary, and primary alkyl bromides upon irradiation with blue light-emitting diodes in the presence of a dual phosphine ligand system. We rationalize that this unprecedented transformation is achieved by utilizing the photoexcited-state reactivity of the palladium complex to enhance oxidative addition and suppress undesired β-hydride elimination.The palladium-catalyzed Mizoroki-Heck reaction is arguably one of the most significant carbon-carbon bond-construction reactions to be discovered in the last 50 years, with a tremendous number of applications in the production of chemicals. This Nobel-Prize-winning transformation has yet to overcome the obstacle of its general application in a range of alkyl electrophiles, especially tertiary alkyl halides that possess eliminable β-hydrogen atoms. Whereas most palladium-catalyzed cross-coupling reactions utilize the ground-state reactivity of palladium complexes under thermal conditions and generally apply a single ligand system, we report that the palladium-catalyzed Heck reaction proceeds smoothly at room temperature with a variety of tertiary, secondary, and primary alkyl bromides upon irradiation with blue light-emitting diodes in the presence of a dual phosphine ligand system. We rationalize that this unprecedented transformation is achieved by utilizing the photoexcited-state reactivity of the palladium complex to enhance oxidative addition and suppress undesired β-hydride elimination. The palladium-catalyzed Mizoroki-Heck reaction is arguably one of the most significant carbon-carbon bond-construction reactions to be discovered in the last 50 years, with a tremendous number of applications in the production of chemicals. This Nobel-Prize-winning transformation has yet to overcome the obstacle of its general application in a range of alkyl electrophiles, especially tertiary alkyl halides that possess eliminable beta-hydrogen atoms. Whereas most palladium-catalyzed cross-coupling reactions utilize the ground-state reactivity of palladium complexes under thermal conditions and generally apply a single ligand system, we report that the palladium-catalyzed Heck reaction proceeds smoothly at room temperature with a variety of tertiary, secondary, and primary alkyl bromides upon irradiation with blue light-emitting diodes in the presence of a dual phosphine ligand system. We rationalize that this unprecedented transformation is achieved by utilizing the photoexcited-state reactivity of the palladium complex to enhance oxidative addition and suppress undesired beta-hydride elimination. |
| Author | Wang, Guang-Zu Cheng, Wan-Min Fu, Yao Shang, Rui |
| AuthorAffiliation | University of Science and Technology of China Hefei National Laboratory for Physical Sciences at the Microscale, CAS Key Laboratory of Urban Pollutant Conversion, Anhui Province Key Laboratory of Biomass Clean Energy, iChEM, Department of Chemistry Department of Chemistry, School of Science The University of Tokyo |
| AuthorAffiliation_xml | – name: University of Science and Technology of China – name: The University of Tokyo – name: Department of Chemistry, School of Science – name: Hefei National Laboratory for Physical Sciences at the Microscale, CAS Key Laboratory of Urban Pollutant Conversion, Anhui Province Key Laboratory of Biomass Clean Energy, iChEM, Department of Chemistry |
| Author_xml | – sequence: 1 givenname: Guang-Zu surname: Wang fullname: Wang, Guang-Zu organization: University of Science and Technology of China – sequence: 2 givenname: Rui orcidid: 0000-0002-2513-2064 surname: Shang fullname: Shang, Rui email: rui@chem.s.u-tokyo.ac.jp organization: The University of Tokyo – sequence: 3 givenname: Wan-Min surname: Cheng fullname: Cheng, Wan-Min organization: University of Science and Technology of China – sequence: 4 givenname: Yao orcidid: 0000-0003-2282-4839 surname: Fu fullname: Fu, Yao email: fuyao@ustc.edu.cn organization: University of Science and Technology of China |
| BackLink | https://www.ncbi.nlm.nih.gov/pubmed/29116777$$D View this record in MEDLINE/PubMed |
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| Snippet | The palladium-catalyzed Mizoroki–Heck reaction is arguably one of the most significant carbon–carbon bond-construction reactions to be discovered in the last... The palladium-catalyzed Mizoroki-Heck reaction is arguably one of the most significant carbon-carbon bond-construction reactions to be discovered in the last... |
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| SubjectTerms | ambient temperature catalytic activity Chemistry Chemistry, Multidisciplinary cross-coupling reactions irradiation Lewis acids ligands light emitting diodes organobromine compounds palladium phosphine Physical Sciences Science & Technology |
| Title | Irradiation-Induced Heck Reaction of Unactivated Alkyl Halides at Room Temperature |
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