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Volumn 696, Issue 1, 2011, Pages 12-15

Regiocontrolled gold(I)-catalyzed cyclization reactions of N-(3-iodoprop-2-ynyl)-N-tosylanilines

Author keywords

Cyclization; Dihydroquinolines; Gold catalyst; Ligand effect

Indexed keywords

ANCILLARY LIGANDS; CYCLIZATION REACTIONS; DIHYDROQUINOLINE; DIHYDROQUINOLINES; GOLD CATALYST; GOLD CATALYSTS; LIGAND EFFECT; REGIOISOMERS; TWO-PRODUCT;

EID: 78649848489     PISSN: 0022328X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jorganchem.2010.09.014     Document Type: Article
Times cited : (40)

References (63)
  • 1
    • 78649840544 scopus 로고    scopus 로고
    • Reviews on hydroarylation of alkynes
    • Reviews on hydroarylation of alkynes:
  • 4
    • 78649872759 scopus 로고    scopus 로고
    • Selected later examples
    • Selected later examples:
  • 13
    • 78649895996 scopus 로고    scopus 로고
    • For representative recent work on alkyne iodoarylation see, for instance
    • For representative recent work on alkyne iodoarylation see, for instance:
  • 16
    • 78649839504 scopus 로고    scopus 로고
    • For a related alkene and allene iodoarylation strategies, see respectively
    • For a related alkene and allene iodoarylation strategies, see respectively:
  • 19
    • 78649902134 scopus 로고    scopus 로고
    • Reports on hydroarylation reactions of alkynes involving gold(III) catalysis
    • Reports on hydroarylation reactions of alkynes involving gold(III) catalysis:
  • 32
    • 78649821716 scopus 로고    scopus 로고
    • 10.1039/c0cc00033g
    • C. Gronnier, Y. Odabachian, and F. Gagosz advance article Chem. Commun. 2010 10.1039/c0cc00033g For alkyne hydroarylation based on the use of cyclic (alkyl)(amino) carbene-gold(I) catalysts [CAAC-gold(I)]
    • (2010) Chem. Commun.
    • Gronnier, C.1    Odabachian, Y.2    Gagosz, F.3
  • 37
    • 78649858863 scopus 로고    scopus 로고
    • For an example of the complementarity of the cycloisomerization versus the iodocyclization approaches involving a different type of ring-closure (cyclization of β-ketoester onto an alkyne, as an illustrative model system) see, for instance: gold(I) catalyzed cyclization
    • For an example of the complementarity of the cycloisomerization versus the iodocyclization approaches involving a different type of ring-closure (cyclization of β-ketoester onto an alkyne, as an illustrative model system) see, for instance: gold(I) catalyzed cyclization.
  • 40
    • 78649899899 scopus 로고    scopus 로고
    • For natural products synthesis based on further manipulation of the assembled vinyliodides using cross-coupling chemistry, see, for instance
    • For natural products synthesis based on further manipulation of the assembled vinyliodides using cross-coupling chemistry, see, for instance:
  • 42
    • 35048843654 scopus 로고    scopus 로고
    • 2-catalyzed cyclization reactions of propargylic tert-butyl carbonates from either the iodoalkynyl precursor or the terminal alkyne in presence of NIS to furnish 4-(iodomethylene)-1,3-dioxolan 2-one derivatives
    • (2007) Angew. Chem. Int. Ed. , vol.46 , pp. 7671-7673
    • Linghu, X.1    Kennedy-Smith, J.J.2    Toste, F.D.3
  • 44
    • 78649855310 scopus 로고    scopus 로고
    • Iodine 1,2-shift, selected examples; ruthenium catalysis
    • Iodine 1,2-shift, selected examples; ruthenium catalysis:
  • 46
    • 0347625830 scopus 로고    scopus 로고
    • H.-C. Shen, S. Pal, J.-J. Lian, and R.-S. Liu J. Am. Chem. Soc. 125 2003 15762 15763 For alternative examples of gold(I)-catalyzed cyclization reaction of iodoalkynes without involving iodine migration see above Reference [5a], see also:
    • (2003) J. Am. Chem. Soc. , vol.125 , pp. 15762-15763
    • Shen, H.-C.1    Pal, S.2    Lian, J.-J.3    Liu, R.-S.4
  • 51
    • 78649855822 scopus 로고    scopus 로고
    • For a review on ligand effects in gold catalysis, see
    • For a review on ligand effects in gold catalysis, see:
  • 55
    • 78649834533 scopus 로고    scopus 로고
    • For late transition metal-NHC complexes in catalysis, see
    • For late transition metal-NHC complexes in catalysis, see:
  • 58
    • 78649850991 scopus 로고    scopus 로고
    • The reaction using as catalyst simply AuCl was tested. However, for this class of starting material the conversion was very poor. For instance, when 1b was treated with AuCl (3mol%, in DCE, for 21 h at rt and under argon) the recovered starting 1b amounts for near 83% (see Ref. [10c]). Notably, for the small amount of cyclization noticed, the distribution was in favour of the product arising from the corresponding 1,2-iodine shift (the 2b:3b ratio was estimated from their nmr integrals to be approximately 1:6).
    • The reaction using as catalyst simply AuCl was tested. However, for this class of starting material the conversion was very poor. For instance, when 1b was treated with AuCl (3mol%, in DCE, for 21 h at rt and under argon) the recovered starting 1b amounts for near 83% (see Ref. [10c]). Notably, for the small amount of cyclization noticed, the distribution was in favour of the product arising from the corresponding 1,2-iodine shift (the 2b:3b ratio was estimated from their nmr integrals to be approximately 1:6).
  • 59
    • 78649831001 scopus 로고    scopus 로고
    • To be published elsewhere.
    • To be published elsewhere.
  • 60
    • 66149185302 scopus 로고    scopus 로고
    • For a nice illustrative example: P.W. Davies, and N. Martin Org. Lett. 11 2009 2293 2296
    • (2009) Org. Lett. , vol.11 , pp. 2293-2296
    • Davies, P.W.1    Martin, N.2
  • 61
    • 78649847573 scopus 로고    scopus 로고
    • For 1,2-halogen migrations in gold-catalyzed reactions involving haloallenyl ketones
    • For 1,2-halogen migrations in gold-catalyzed reactions involving haloallenyl ketones:


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.