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Volumn 132, Issue 38, 2010, Pages 13117-13119

Nickel-catalyzed alkenylative cross-coupling reaction of alkyl sulfides

Author keywords

[No Author keywords available]

Indexed keywords

ALKENYL; ALKYL SULFIDES; ARYL SULFIDES; COUPLING PRODUCT; CROSS COUPLING REACTIONS; GRIGNARD REAGENT; HIGH YIELD; N-HETEROCYCLIC CARBENE LIGANDS;

EID: 77957140669     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja104155f     Document Type: Article
Times cited : (40)

References (41)
  • 1
    • 77957174312 scopus 로고    scopus 로고
    • For reviews, see
    • For reviews, see
  • 5
    • 77957163227 scopus 로고    scopus 로고
    • For the first report on the reaction of aryl sulfides, see
    • For the first report on the reaction of aryl sulfides, see
  • 7
    • 77957142257 scopus 로고    scopus 로고
    • For the first report on the reaction of heteroaryl sulfide, see
    • For the first report on the reaction of heteroaryl sulfide, see
  • 9
    • 77957138556 scopus 로고    scopus 로고
    • For the smell of alkanethiols, see
    • For the smell of alkanethiols, see
  • 11
    • 77957117798 scopus 로고    scopus 로고
    • For selected cross-coupling reactions of alkyl aryl sulfides, see
    • For selected cross-coupling reactions of alkyl aryl sulfides, see
  • 20
    • 77957107995 scopus 로고    scopus 로고
    • For the industrial supply of sulfur, see
    • For the industrial supply of sulfur, see
  • 22
    • 77957111669 scopus 로고    scopus 로고
    • For reactions of dithioacetals with Grignard reagents giving olefins, see
    • For reactions of dithioacetals with Grignard reagents giving olefins, see
  • 25
    • 77957168713 scopus 로고    scopus 로고
    • The use of dodecanethiol instead of dodecyl phenyl sulfide did not give the alkenylative coupling product 2 but the conventional coupling product, 1-dodecyl-4-methylbenzene (7%), dodecane (24%), and 1-dodecene (27%), respectively
    • The use of dodecanethiol instead of dodecyl phenyl sulfide did not give the alkenylative coupling product 2 but the conventional coupling product, 1-dodecyl-4-methylbenzene (7%), dodecane (24%), and 1-dodecene (27%), respectively.
  • 26
    • 77957169093 scopus 로고    scopus 로고
    • The reaction of 2,2,4,4,6,6-hexamethyl-1,3,5-trithiane, a trimer form of propane-2-thione, with 4-(N, N-dimethylamino)phenyl Grignard reagent gave the corresponding alkenylative coupling product, N, N-dimethyl-4-(prop-1-en-2-yl) aniline (17%) with recovery of the trithiane (51%), which indicates an intermediacy of thioketone in the present alkenylative coupling reaction
    • The reaction of 2,2,4,4,6,6-hexamethyl-1,3,5-trithiane, a trimer form of propane-2-thione, with 4-(N, N-dimethylamino)phenyl Grignard reagent gave the corresponding alkenylative coupling product, N, N-dimethyl-4-(prop-1-en-2-yl) aniline (17%) with recovery of the trithiane (51%), which indicates an intermediacy of thioketone in the present alkenylative coupling reaction.
  • 27
    • 77957173516 scopus 로고    scopus 로고
    • See the Supporting Information for details
    • See the Supporting Information for details.
  • 28
    • 77957108377 scopus 로고    scopus 로고
    • For the deprotonation of thiocarbonyl compounds, see
    • For the deprotonation of thiocarbonyl compounds, see
  • 31
    • 77957119078 scopus 로고    scopus 로고
    • For the tautomerization of thiocarbonyl compounds, see
    • For the tautomerization of thiocarbonyl compounds, see
  • 33
    • 77957155233 scopus 로고    scopus 로고
    • For cross-couplings of aryl thiolates, see
    • For cross-couplings of aryl thiolates, see
  • 36
    • 77957106900 scopus 로고    scopus 로고
    • For generation of MgS, see
    • For generation of MgS, see
  • 38
    • 77957144517 scopus 로고    scopus 로고
    • For addition of Grignard reagents to thioketone, see
    • For addition of Grignard reagents to thioketone, see
  • 40
    • 77957144649 scopus 로고    scopus 로고
    • The reaction of naphthalene-2-ylmethanethiol with 3 equiv of p-tolyl Grignard reagent under the present reaction conditions gave the coupling product, 2-(4-methylbenzyl)naphthalene (35%), and the reduced product, 2-methyl naphthalene (27%). For geminal dimethylation of dithioacetals, see
    • The reaction of naphthalene-2-ylmethanethiol with 3 equiv of p-tolyl Grignard reagent under the present reaction conditions gave the coupling product, 2-(4-methylbenzyl)naphthalene (35%), and the reduced product, 2-methyl naphthalene (27%). For geminal dimethylation of dithioacetals, see


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.