메뉴 건너뛰기




Volumn 51, Issue 17, 2012, Pages 4122-4127

Regio- and stereocontrolled introduction of secondary alkyl groups to electron-deficient arenes through copper-catalyzed allylic alkylation

Author keywords

allylic alkylation; azoles; copper; heteroarenes; regioselectivity

Indexed keywords

ALKYL GROUPS; ALLYLIC ALKYLATION; ALLYLIC PHOSPHATES; AROMATIC RINGS; AZOLES; ELECTRON-DEFICIENT; FLUOROARENES; HETEROARENES; MILD REACTION CONDITIONS; PYRIDINE N-OXIDE; STEREOGENIC CENTERS;

EID: 84859965961     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201200809     Document Type: Article
Times cited : (105)

References (81)
  • 2
    • 9644264170 scopus 로고    scopus 로고
    • V. S. C. Yeh, Tetrahedron 2004, 60, 11995-12042
    • (2004) Tetrahedron , vol.60 , pp. 11995-12042
    • Yeh, V.S.C.1
  • 6
    • 33746216322 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2006, 45, 2958-2961, and references therein.
    • (2006) Angew. Chem. Int. Ed. , vol.45 , pp. 2958-2961
  • 10
    • 71949117774 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2009, 48, 9608-9644.
    • (2009) Angew. Chem. Int. Ed. , vol.48 , pp. 9608-9644
  • 17
    • 77953682528 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2010, 49, 4451-4454
    • (2010) Angew. Chem. Int. Ed. , vol.49 , pp. 4451-4454
  • 20
    • 79851483350 scopus 로고    scopus 로고
    • K. Gao, N. Yoshikai, J. Am. Chem. Soc. 2011, 133, 400-402; For the secondary alkylation of phenols by the Re-catalyzed hydroarylation of alkenes, see
    • (2011) J. Am. Chem. Soc. , vol.133 , pp. 400-402
    • Gao, K.1    Yoshikai, N.2
  • 22
    • 77954079821 scopus 로고    scopus 로고
    • For a review on transition-metal-catalyzed C sp 2 H alkylations of (hetero)arenes with alkyl halides, see:, L. Ackermann, Chem. Commun. 2010, 46, 4866-4877.
    • (2010) Chem. Commun. , vol.46 , pp. 4866-4877
    • Ackermann, L.1
  • 24
    • 77951159576 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2010, 49, 3061-3064
    • (2010) Angew. Chem. Int. Ed. , vol.49 , pp. 3061-3064
  • 28
    • 84255198425 scopus 로고    scopus 로고
    • L. Ackermann, B. Punji, W. Song, Adv. Synth. Catal. 2011, 353, 3325-3329; for Ru-catalyzed C sp 2 H alkylations of arenes with primary or secondary alkyl halides, see
    • (2011) Adv. Synth. Catal. , vol.353 , pp. 3325-3329
    • Ackermann, L.1    Punji, B.2    Song, W.3
  • 30
    • 70349779001 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2009, 48, 6045-6048; for transition-metal-catalyzed (with Pd or Ru) benzylations of (hetero)arenes with primary benzylic electrophiles, see
    • (2009) Angew. Chem. Int. Ed. , vol.48 , pp. 6045-6048
  • 40
    • 79952611097 scopus 로고    scopus 로고
    • X. Zhao, G. Wu, Y. Zhang, J. Wang, J. Am. Chem. Soc. 2011, 133, 3296-3299; Hirano, Miura and co-workers reported secondary alkylation of 1,3-azoles through Co- and Ni-catalyzed reactions with N-tosylhydrazones
    • (2011) J. Am. Chem. Soc. , vol.133 , pp. 3296-3299
    • Zhao, X.1    Wu, G.2    Zhang, Y.3    Wang, J.4
  • 42
  • 58
    • 73249152382 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2009, 48, 9553-9556
    • (2009) Angew. Chem. Int. Ed. , vol.48 , pp. 9553-9556
  • 62
    • 79959206488 scopus 로고    scopus 로고
    • Recently, Hirano, Miura, and co-workers reported the Cu-catalyzed C sp 2 H allylation of fluoroarenes with allylic phosphates. The introduction of secondary alkyl groups to fluoroarenes was specifically described for the case of 2-cycloheptenyl phosphate. Under their conditions, the reaction of an asymmetrically 1,3-disubstituted secondary allylic phosphate with pentafluorobenzene was not regiocontrolled
    • Recently, Hirano, Miura, and co-workers reported the Cu-catalyzed C sp 2 H allylation of fluoroarenes with allylic phosphates. The introduction of secondary alkyl groups to fluoroarenes was specifically described for the case of 2-cycloheptenyl phosphate. Under their conditions, the reaction of an asymmetrically 1,3-disubstituted secondary allylic phosphate with pentafluorobenzene was not regiocontrolled:, T. Yao, K. Hirano, T. Satoh, M. Miura, Angew. Chem. 2011, 123, 3046-3050
    • (2011) Angew. Chem. , vol.123 , pp. 3046-3050
    • Yao, T.1    Hirano, K.2    Satoh, T.3    Miura, M.4
  • 63
    • 79952655564 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2011, 50, 2990-2994.
    • (2011) Angew. Chem. Int. Ed. , vol.50 , pp. 2990-2994
  • 64
    • 84859997897 scopus 로고    scopus 로고
    • Recently, Zhang and co-workers reported a Pd and Cu co-catalyzed method for C sp 2 H primary allylation of fluoroarenes with allylic carbonates. A secondary alkylation product was described only as a minor by-product in the formation of a primary allylation product
    • Recently, Zhang and co-workers reported a Pd and Cu co-catalyzed method for C sp 2 H primary allylation of fluoroarenes with allylic carbonates. A secondary alkylation product was described only as a minor by-product in the formation of a primary allylation product:, S. Fan, F. Chen, X. Zhang, Angew. Chem. 2011, 123, 6040-6045
    • (2011) Angew. Chem. , vol.123 , pp. 6040-6045
    • Fan, S.1    Chen, F.2    Zhang, X.3
  • 65
    • 79959251312 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2011, 50, 5918-5923.
    • (2011) Angew. Chem. Int. Ed. , vol.50 , pp. 5918-5923
  • 71
    • 34250704681 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2007, 46, 4554-4558
    • (2007) Angew. Chem. Int. Ed. , vol.46 , pp. 4554-4558
  • 74
    • 70350599360 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2009, 48, 8733-8735
    • (2009) Angew. Chem. Int. Ed. , vol.48 , pp. 8733-8735
  • 78
    • 78149439210 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2010, 49, 8370-8374.
    • (2010) Angew. Chem. Int. Ed. , vol.49 , pp. 8370-8374


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.