Preparation of naphthalenes via Pd‐catalyzed annulation of 5‐(2‐bromophenyl)pent‐3‐en‐1‐ynes under Suzuki‐Miyaura coupling conditions
Highly substituted naphthalene derivatives were prepared via palladium‐catalyzed reaction of 5‐(2‐bromophenyl)pent‐3‐en‐1‐ynes with arylboronic acids. Typically, reaction of 3‐bromo‐4‐(3‐(4‐chlorophenyl)‐5‐phenyl‐1‐(p‐tolyl)pent‐2‐en‐4‐yn‐1‐yl)‐N‐methylaniline (1a) with PhB(OH)2 in the presence of P...
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| Published in: | Journal of the Chinese Chemical Society (Taipei) Vol. 71; no. 10; pp. 1300 - 1308 |
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01-10-2024
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| Abstract | Highly substituted naphthalene derivatives were prepared via palladium‐catalyzed reaction of 5‐(2‐bromophenyl)pent‐3‐en‐1‐ynes with arylboronic acids. Typically, reaction of 3‐bromo‐4‐(3‐(4‐chlorophenyl)‐5‐phenyl‐1‐(p‐tolyl)pent‐2‐en‐4‐yn‐1‐yl)‐N‐methylaniline (1a) with PhB(OH)2 in the presence of Pd(PPh3)4 as the catalyst under basic conditions provided 8‐benzhydryl‐7‐(4‐chlorophenyl)‐N‐methyl‐5‐(p‐tolyl)naphthalen‐2‐amine (2a) quantitatively. Overall, 19 new naphthalene compounds were obtained by this methodology and their structures were characterized by spectroscopic methods. In addition, crystal structure of 2j was determined to confirm the structural details. Reaction pathway leading to the desired product is also discussed.
Using palladium‐catalyzed reaction of 5‐(2‐bromophenyl)pent‐3‐en‐1‐ynes with arylboronic acids was studied. Reaction proceeds with C‐Br bond activation, migratory insertion, metathesis with arylboronate, and reductive elimination to yield the desired naphthalene derivatives. |
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| AbstractList | Highly substituted naphthalene derivatives were prepared via palladium‐catalyzed reaction of 5‐(2‐bromophenyl)pent‐3‐en‐1‐ynes with arylboronic acids. Typically, reaction of 3‐bromo‐4‐(3‐(4‐chlorophenyl)‐5‐phenyl‐1‐( p ‐tolyl)pent‐2‐en‐4‐yn‐1‐yl)‐ N ‐methylaniline ( 1a ) with PhB(OH) 2 in the presence of Pd(PPh 3 ) 4 as the catalyst under basic conditions provided 8‐benzhydryl‐7‐(4‐chlorophenyl)‐ N ‐methyl‐5‐( p‐ tolyl)naphthalen‐2‐amine ( 2a ) quantitatively. Overall, 19 new naphthalene compounds were obtained by this methodology and their structures were characterized by spectroscopic methods. In addition, crystal structure of 2j was determined to confirm the structural details. Reaction pathway leading to the desired product is also discussed. Highly substituted naphthalene derivatives were prepared via palladium‐catalyzed reaction of 5‐(2‐bromophenyl)pent‐3‐en‐1‐ynes with arylboronic acids. Typically, reaction of 3‐bromo‐4‐(3‐(4‐chlorophenyl)‐5‐phenyl‐1‐(p‐tolyl)pent‐2‐en‐4‐yn‐1‐yl)‐N‐methylaniline (1a) with PhB(OH)2 in the presence of Pd(PPh3)4 as the catalyst under basic conditions provided 8‐benzhydryl‐7‐(4‐chlorophenyl)‐N‐methyl‐5‐(p‐tolyl)naphthalen‐2‐amine (2a) quantitatively. Overall, 19 new naphthalene compounds were obtained by this methodology and their structures were characterized by spectroscopic methods. In addition, crystal structure of 2j was determined to confirm the structural details. Reaction pathway leading to the desired product is also discussed. Highly substituted naphthalene derivatives were prepared via palladium‐catalyzed reaction of 5‐(2‐bromophenyl)pent‐3‐en‐1‐ynes with arylboronic acids. Typically, reaction of 3‐bromo‐4‐(3‐(4‐chlorophenyl)‐5‐phenyl‐1‐(p‐tolyl)pent‐2‐en‐4‐yn‐1‐yl)‐N‐methylaniline (1a) with PhB(OH)2 in the presence of Pd(PPh3)4 as the catalyst under basic conditions provided 8‐benzhydryl‐7‐(4‐chlorophenyl)‐N‐methyl‐5‐(p‐tolyl)naphthalen‐2‐amine (2a) quantitatively. Overall, 19 new naphthalene compounds were obtained by this methodology and their structures were characterized by spectroscopic methods. In addition, crystal structure of 2j was determined to confirm the structural details. Reaction pathway leading to the desired product is also discussed. Using palladium‐catalyzed reaction of 5‐(2‐bromophenyl)pent‐3‐en‐1‐ynes with arylboronic acids was studied. Reaction proceeds with C‐Br bond activation, migratory insertion, metathesis with arylboronate, and reductive elimination to yield the desired naphthalene derivatives. |
| Author | Liu, Yi‐Hung Hsu, Cheng‐Kai Liu, Shiuh‐Tzung |
| Author_xml | – sequence: 1 givenname: Cheng‐Kai surname: Hsu fullname: Hsu, Cheng‐Kai organization: National Taiwan University – sequence: 2 givenname: Yi‐Hung surname: Liu fullname: Liu, Yi‐Hung organization: National Taiwan University – sequence: 3 givenname: Shiuh‐Tzung orcidid: 0000-0002-0544-006X surname: Liu fullname: Liu, Shiuh‐Tzung email: stliu@ntu.edu.tw organization: National Taiwan University |
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| Snippet | Highly substituted naphthalene derivatives were prepared via palladium‐catalyzed reaction of 5‐(2‐bromophenyl)pent‐3‐en‐1‐ynes with arylboronic acids.... |
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| SubjectTerms | Chemical reactions coupling Crystal structure cyclization enyne Naphthalene Palladium |
| Title | Preparation of naphthalenes via Pd‐catalyzed annulation of 5‐(2‐bromophenyl)pent‐3‐en‐1‐ynes under Suzuki‐Miyaura coupling conditions |
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