Synthetic and Mechanistic Studies on Pd(0)-Catalyzed Diamination of Conjugated Dienes
Various dienes and a triene can be regioselectively diaminated at the internal double bond with good yields and high diastereoselectivity using di-tert-butyldiaziridinone (5) as the nitrogen source and Pd(PPh3)4 (1−10 mol %) as the catalyst. Kinetic studies with 1H NMR spectroscopy show that the dia...
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| Published in | Journal of the American Chemical Society Vol. 132; no. 10; pp. 3523 - 3532 |
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| Main Authors | , , , |
| Format | Journal Article |
| Language | English |
| Published |
United States
American Chemical Society
17.03.2010
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| Subjects | |
| Online Access | Get full text |
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| Abstract | Various dienes and a triene can be regioselectively diaminated at the internal double bond with good yields and high diastereoselectivity using di-tert-butyldiaziridinone (5) as the nitrogen source and Pd(PPh3)4 (1−10 mol %) as the catalyst. Kinetic studies with 1H NMR spectroscopy show that the diamination is first-order in total Pd catalyst and inverse first-order in PPh3. For reactive dienes, such as 1-methoxybutadiene (6g) and alkyl 1,3-butadienes (6a, 6j), the diamination is first-order in di-tert-butyldiaziridinone (5) and zero-order in the olefin. For olefins with relatively low reactivity, such as (E)-1-phenylbutadiene (6b) and (3E,5E)-1,3,5-decatriene (6i), similar diamination rates were observed when 3.5 equiv of olefins were used. Pd(PPh3)2 is likely to be the active species for the insertion of Pd(0) into the N−N bond of di-tert-butyldiaziridinone (5) to form a four-membered Pd(II) complex (A), which can be detected by NMR spectroscopy. The olefin complex (B), formed from intermediate A via ligand exchange between the olefin substrate and the PPh3, undergoes migratory insertion and reductive elimination to give the diamination product and regenerate the Pd(0) catalyst. |
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| AbstractList | Various dienes and a triene can be regioselectively diaminated at the internal double bond with good yields and high diastereoselectivity using di-tert-butyldiaziridinone (5) as the nitrogen source and Pd(PPh(3))(4) (1-10 mol %) as the catalyst. Kinetic studies with (1)H NMR spectroscopy show that the diamination is first-order in total Pd catalyst and inverse first-order in PPh(3). For reactive dienes, such as 1-methoxybutadiene (6g) and alkyl 1,3-butadienes (6a, 6j), the diamination is first-order in di-tert-butyldiaziridinone (5) and zero-order in the olefin. For olefins with relatively low reactivity, such as (E)-1-phenylbutadiene (6b) and (3E,5E)-1,3,5-decatriene (6i), similar diamination rates were observed when 3.5 equiv of olefins were used. Pd(PPh(3))(2) is likely to be the active species for the insertion of Pd(0) into the N-N bond of di-tert-butyldiaziridinone (5) to form a four-membered Pd(II) complex (A), which can be detected by NMR spectroscopy. The olefin complex (B), formed from intermediate A via ligand exchange between the olefin substrate and the PPh(3), undergoes migratory insertion and reductive elimination to give the diamination product and regenerate the Pd(0) catalyst.Various dienes and a triene can be regioselectively diaminated at the internal double bond with good yields and high diastereoselectivity using di-tert-butyldiaziridinone (5) as the nitrogen source and Pd(PPh(3))(4) (1-10 mol %) as the catalyst. Kinetic studies with (1)H NMR spectroscopy show that the diamination is first-order in total Pd catalyst and inverse first-order in PPh(3). For reactive dienes, such as 1-methoxybutadiene (6g) and alkyl 1,3-butadienes (6a, 6j), the diamination is first-order in di-tert-butyldiaziridinone (5) and zero-order in the olefin. For olefins with relatively low reactivity, such as (E)-1-phenylbutadiene (6b) and (3E,5E)-1,3,5-decatriene (6i), similar diamination rates were observed when 3.5 equiv of olefins were used. Pd(PPh(3))(2) is likely to be the active species for the insertion of Pd(0) into the N-N bond of di-tert-butyldiaziridinone (5) to form a four-membered Pd(II) complex (A), which can be detected by NMR spectroscopy. The olefin complex (B), formed from intermediate A via ligand exchange between the olefin substrate and the PPh(3), undergoes migratory insertion and reductive elimination to give the diamination product and regenerate the Pd(0) catalyst. Various dienes and a triene can be regioselectively diaminated at the internal double bond with good yields and high diastereoselectivity using di-tert-butyldiaziridinone (5) as the nitrogen source and Pd(PPh3)4 (1−10 mol %) as the catalyst. Kinetic studies with 1H NMR spectroscopy show that the diamination is first-order in total Pd catalyst and inverse first-order in PPh3. For reactive dienes, such as 1-methoxybutadiene (6g) and alkyl 1,3-butadienes (6a, 6j), the diamination is first-order in di-tert-butyldiaziridinone (5) and zero-order in the olefin. For olefins with relatively low reactivity, such as (E)-1-phenylbutadiene (6b) and (3E,5E)-1,3,5-decatriene (6i), similar diamination rates were observed when 3.5 equiv of olefins were used. Pd(PPh3)2 is likely to be the active species for the insertion of Pd(0) into the N−N bond of di-tert-butyldiaziridinone (5) to form a four-membered Pd(II) complex (A), which can be detected by NMR spectroscopy. The olefin complex (B), formed from intermediate A via ligand exchange between the olefin substrate and the PPh3, undergoes migratory insertion and reductive elimination to give the diamination product and regenerate the Pd(0) catalyst. Various dienes and a triene can be regioselectively diaminated at the internal double bond with good yields and high diastereoselectivity using di- tert -butyldiaziridinone ( 5 ) as nitrogen source and Pd(PPh 3 ) 4 (1–10 mol%) as catalyst. Kinetic studies with 1 H NMR spectroscopy show that the diamination is first-order in total Pd catalyst and inverse first-order in PPh 3 . For reactive dienes, such as 1-methoxybutadiene ( 6g ) and alkyl 1,3-butadienes ( 6a , 6j ), the diamination is first order in di- tert -butyldiaziridinone ( 5 ) and zero-order in the olefin. For olefins with relatively low reactivity, such as ( E )-1-phenyl-butadiene ( 6b ) and ( 3E , 5E )-1,3,5-decatriene ( 6i ), similar diamination rates were observed when 3.5 equivalents of olefins were used. Pd(PPh 3 ) 2 is likely to be the active species for the insertion of Pd(0) into the N-N bond of di- tert -butyldiaziridinone ( 5 ) to form a four-membered Pd(II) complex ( A) , which can be detected by NMR spectroscopy. Olefin complex ( B ), formed from intermediate A via ligand exchange between the olefin substrate and the PPh 3, undergoes migratory insertion and reductive elimination to give the diamination product and regenerate the Pd(0) catalyst. Various dienes and a triene can be regioselectively diaminated at the internal double bond with good yields and high diastereoselectivity using di-tert-butyldiaziridinone (5) as the nitrogen source and Pd(PPh(3))(4) (1-10 mol %) as the catalyst. Kinetic studies with (1)H NMR spectroscopy show that the diamination is first-order in total Pd catalyst and inverse first-order in PPh(3). For reactive dienes, such as 1-methoxybutadiene (6g) and alkyl 1,3-butadienes (6a, 6j), the diamination is first-order in di-tert-butyldiaziridinone (5) and zero-order in the olefin. For olefins with relatively low reactivity, such as (E)-1-phenylbutadiene (6b) and (3E,5E)-1,3,5-decatriene (6i), similar diamination rates were observed when 3.5 equiv of olefins were used. Pd(PPh(3))(2) is likely to be the active species for the insertion of Pd(0) into the N-N bond of di-tert-butyldiaziridinone (5) to form a four-membered Pd(II) complex (A), which can be detected by NMR spectroscopy. The olefin complex (B), formed from intermediate A via ligand exchange between the olefin substrate and the PPh(3), undergoes migratory insertion and reductive elimination to give the diamination product and regenerate the Pd(0) catalyst. |
| Author | Zhao, Baoguo Du, Haifeng Cui, Sunliang Shi, Yian |
| Author_xml | – sequence: 1 givenname: Baoguo surname: Zhao fullname: Zhao, Baoguo – sequence: 2 givenname: Haifeng surname: Du fullname: Du, Haifeng – sequence: 3 givenname: Sunliang surname: Cui fullname: Cui, Sunliang – sequence: 4 givenname: Yian surname: Shi fullname: Shi, Yian email: yian@lamar.colostate.edu |
| BackLink | https://www.ncbi.nlm.nih.gov/pubmed/20166669$$D View this record in MEDLINE/PubMed |
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| Snippet | Various dienes and a triene can be regioselectively diaminated at the internal double bond with good yields and high diastereoselectivity using... Various dienes and a triene can be regioselectively diaminated at the internal double bond with good yields and high diastereoselectivity using di- tert... |
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| SubjectTerms | Alkadienes - chemistry Amination Aziridines - chemistry Catalysis Diamines - chemical synthesis Kinetics Magnetic Resonance Spectroscopy - methods Organophosphorus Compounds - chemistry Palladium - chemistry |
| Title | Synthetic and Mechanistic Studies on Pd(0)-Catalyzed Diamination of Conjugated Dienes |
| URI | http://dx.doi.org/10.1021/ja909459h https://www.ncbi.nlm.nih.gov/pubmed/20166669 https://www.proquest.com/docview/733473438 https://pubmed.ncbi.nlm.nih.gov/PMC2846102 |
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