Nickel-catalyzed direct arylation of azoles with aryl bromides

Organic Letters

Volumn 11, Issue 8, 2009, Pages 1737-1740

  Hachiya, Hitoshi ^a   Hirano, Koji ^a   Satoh, Tetsuya ^a   Miura, Masahiro ^a  

^a OSAKA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

BROMINATED HYDROCARBON; NICKEL; OXAZOLE DERIVATIVE; PYRROLE DERIVATIVE; THIAZOLE DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; COMBINATORIAL CHEMISTRY; SYNTHESIS;

AZOLES; CATALYSIS; COMBINATORIAL CHEMISTRY TECHNIQUES; HYDROCARBONS, BROMINATED; MOLECULAR STRUCTURE; NICKEL; OXAZOLES; THIAZOLES;

EID: 65249095692     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol900159a     Document Type: Article

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35. Exceptionally highly reactive aryl bromides such as 2-bromopyridine were available for use in the copper-catalyzed direct arylation. See ref 6b.
36. 3 showed no catalytic activities. Dppbz in diglyme was unexpectedly not effective.
37. In the reaction of benzothiazole (1), the addition of Zn powder gave no effect on yield. Hence, the combination of 1 and LiO-f-Bu in diglyme would reduce the divalent nickel source to the corresponding zerovalent active species effectively (see Scheme 2).
38. As observed in the reaction of benzoxazole (4), the addition of Zn powder improved the yield. For example, without Zn powder, compound 7bl was obtained in 79% yield.
39. In the reaction mixture, a small amount of the homocoupling product of benzothiazole was detected by GC-MS analysis.
40. Deprotonation of heterocyclic compounds with LiO-f-Bu was suggested. Do, H.-Q.; Daugulis. O.'Org. Lett. 2009, 11, 421 See also ref 6. Nevertheless, at this stage, the pathway involving nickel-assisted proton abstraction mechanism could not be completely excluded.