Stereodefined synthesis of a new type of 1,3-dienes by ligand-controlled carbon-carbon and carbon-heteroatom bond formation in nickel-catalyzed reaction of diaryldichalcogenides with alkynes

Organometallics

Volumn 27, Issue 16, 2008, Pages 4056-4061

  Ananikov, Valentine P ^a   Orlov, Nikolay V ^a   Kabeshov, Mikhail A ^a   Beletskaya, Irina P ^b   Starikova, Zoya A ^c  

^a N D ZELINSKY INSTITUTE OF ORGANIC CHEMISTRY   (Russian Federation)

^b MOSCOW STATE UNIVERSITY   (Russian Federation)

^c A N NESMEYANOV INSTITUTE OF ORGANOELEMENT COMPOUNDS   (Russian Federation)

Author keywords

[No Author keywords available]

Indexed keywords

ACETYLENE; CHELATION; HYDROCARBONS; ISOMERS; LIGANDS; NICKEL; NICKEL ALLOYS; ORGANIC POLYMERS; SELENIUM; STEEL BEAMS AND GIRDERS; SULFUR; VIBRATIONS (MECHANICAL);

BOND FORMATIONS; HETERO ATOMS; UNSYMMETRICAL;

CARBON;

EID: 51049085807     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om800282h     Document Type: Article

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57. See the Supporting Information for more details.
58. See the Supporting Information for a detailed description of a reliable choice of solvent, temperature, etc.
59. Several experimental studies have shown that insertion of terminal alkynes into the M-E bond (E = S, Se) is highly regioselective and leads to M-CH=C(R)E species, while the formation of M-CR=C(H)E species was not observed (see ref 5). Therefore, this pathway was not examined in our theoretical study.
60. The calculations were carried out using the B3LYP density functional level with the Stuttgart/Dresden ECP basis set on the metal and the 6-311G(d) basis set on the other elements (see the Supporting Information for a complete description). In the previous studies it was established that this level of theory reasonably well describes the energy and geometry parameters of the systems involving transition metal complexes:(a) Ananikov, V. P.; Musaev, D. G.; Morokuma, K. J. Am. Chem. Soc. 2002, 124, 2839.
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62. There are two possible reasons for the observed stability of the s-gauche conformation: (1) thermodynamic reasons; for the synthesized dienes the s-gauche conformation is lower in energy than s-trans; and (2) kinetic reasons; the high energy barrier of rotation around the central C-C bond. The key difference between dienes 2 and 3 is the presence of substituent R in the 3-position of 2, which should enhance the influence of both above-mentioned factors.