Tags

Type your tag names separated by a space and hit enter

Nickel-catalyzed dehydrogenative [4 + 2] cycloaddition of 1,3-dienes with nitriles.
J Am Chem Soc. 2011 Nov 16; 133(45):18018-21.JA

Abstract

Pyridines, which comprise one of the most important classes of the six-membered heterocyclic compounds, are widely distributed in nature, and the transition-metal-catalyzed [2 + 2 + 2] cycloaddition reaction of two alkynes and a nitrile is one of the most powerful methods for preparing versatile, highly substituted pyridine derivatives. However, the lack of chemo- and regioselectivity is still a crucial issue associated with fully intermolecular [2 + 2 + 2] cycloaddition. The present study developed the Ni(0)-catalyzed intermolecular dehydrogenative [4 + 2] cycloaddition reaction of 1,3-butadienes with nitriles to give a variety of pyridines regioselectively.

Links

Publisher Full Text (DOI)

Authors+Show Affiliations

Ohashi M
Department of Applied Chemistry, Faculty of Engineering, Osaka University, Suita, Osaka 565-0871, Japan.
Takeda I
No affiliation info available
Ikawa M
No affiliation info available
Ogoshi S
No affiliation info available

MeSH

ButadienesCatalysisCrystallography, X-RayCyclizationHydrogenationModels, MolecularMolecular StructureNickelNitrilesOrganometallic CompoundsPyridinesStereoisomerism

Pub Type(s)

Journal Article
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

22003886

Citation

Ohashi, Masato, et al. "Nickel-catalyzed Dehydrogenative [4 + 2] Cycloaddition of 1,3-dienes With Nitriles." Journal of the American Chemical Society, vol. 133, no. 45, 2011, pp. 18018-21.
Ohashi M, Takeda I, Ikawa M, et al. Nickel-catalyzed dehydrogenative [4 + 2] cycloaddition of 1,3-dienes with nitriles. J Am Chem Soc. 2011;133(45):18018-21.
Ohashi, M., Takeda, I., Ikawa, M., & Ogoshi, S. (2011). Nickel-catalyzed dehydrogenative [4 + 2] cycloaddition of 1,3-dienes with nitriles. Journal of the American Chemical Society, 133(45), 18018-21. https://doi.org/10.1021/ja208162w
Ohashi M, et al. Nickel-catalyzed Dehydrogenative [4 + 2] Cycloaddition of 1,3-dienes With Nitriles. J Am Chem Soc. 2011 Nov 16;133(45):18018-21. PubMed PMID: 22003886.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Nickel-catalyzed dehydrogenative [4 + 2] cycloaddition of 1,3-dienes with nitriles. AU - Ohashi,Masato, AU - Takeda,Ippei, AU - Ikawa,Masashi, AU - Ogoshi,Sensuke, Y1 - 2011/10/21/ PY - 2011/10/19/entrez PY - 2011/10/19/pubmed PY - 2012/3/8/medline SP - 18018 EP - 21 JF - Journal of the American Chemical Society JO - J Am Chem Soc VL - 133 IS - 45 N2 - Pyridines, which comprise one of the most important classes of the six-membered heterocyclic compounds, are widely distributed in nature, and the transition-metal-catalyzed [2 + 2 + 2] cycloaddition reaction of two alkynes and a nitrile is one of the most powerful methods for preparing versatile, highly substituted pyridine derivatives. However, the lack of chemo- and regioselectivity is still a crucial issue associated with fully intermolecular [2 + 2 + 2] cycloaddition. The present study developed the Ni(0)-catalyzed intermolecular dehydrogenative [4 + 2] cycloaddition reaction of 1,3-butadienes with nitriles to give a variety of pyridines regioselectively. SN - 1520-5126 UR - https://www.unboundmedicine.com/medline/citation/22003886/Nickel_catalyzed_dehydrogenative_[4_+_2]_cycloaddition_of_13_dienes_with_nitriles_ L2 - https://doi.org/10.1021/ja208162w DB - PRIME DP - Unbound Medicine ER -