메뉴 건너뛰기




Volumn 60, Issue 2, 2004, Pages 367-381

Transformation of β-chalcogeno alkenylboranes into tetrasubstituted olefins

Author keywords

Alkenylboranes; Nickel catalyzed coupling with Grignard reagents; Rearrangement of 1 alkynyltrialkyl borates; Suzuki Miyaura coupling; Tetrasubstituted olefins; Transmetalation; Trisubstituted vinyl chalcogenides

Indexed keywords

4 ETHYL 5 PHENYL 1,4 DECADIENE; 4 ETHYL 5 PHENYL 4 DECENE; 5 BENZYL 6 METHYL 5 DECENE; 5 BUTYL 6 METHYL 5 DECENE; 5 ETHYL 6 PHENYL 5 DECENE; ALKENE DERIVATIVE; BORANE DERIVATIVE; BORON; CHALCOGEN; COPPER; SULFIDE; UNCLASSIFIED DRUG;

EID: 0346256824     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2003.11.023     Document Type: Article
Times cited : (22)

References (32)
  • 7
    • 0001457755 scopus 로고
    • This reaction is probably the selenium analogue of the Pd-catalyzed substitution of aromatic halides by thiolates:
    • This reaction is probably the selenium analogue of the Pd-catalyzed substitution of aromatic halides by thiolates: Migita T., Shimizu T., Asami Y., Shiobara J.-I., Kato Y., Kosugi M. Bull. Chem. Soc. Jpn. 53:1980;1385.
    • (1980) Bull. Chem. Soc. Jpn , vol.53 , pp. 1385
    • Migita, T.1    Shimizu, T.2    Asami, Y.3    Shiobara, J.-I.4    Kato, Y.5    Kosugi, M.6
  • 8
    • 85030932227 scopus 로고    scopus 로고
    • note
    • See Ref. 1 and references therein.
  • 10
    • 0007802928 scopus 로고
    • Such catalysis does have precedents: (a) Yatagai H., Yamamoto Y., Maruyama K. J. Chem. Soc., Chem. Commun. 1978;702 (b) Yatagai H. Bull. Chem. Soc. Jpn. 53:1980;1670.
    • (1980) Bull. Chem. Soc. Jpn , vol.53 , pp. 1670
    • Yatagai, H.1
  • 17
    • 0004246896 scopus 로고    scopus 로고
    • For a review, see: (a) Knochel P., Betzemeier B. Krause N. Modern organocopper chemistry. 2002;51-53 Wiley-VCH, Weinheim. see also: (b) Miyaura N., Itoh M., Suzuki A. Synthesis. 1976;618 (c) Brown H.C., Campbell J.B. Jr. J. Org. Chem. 45:1980;550 (d) Yatagai H. J. Org. Chem. 45:1980;1640 (e) Hoshi M., Masuda Y., Arase A. Bull. Chem. Soc. Jpn. 59:1986;659 (f) Wang K.K., Chu K.-H., Lin Y., Chen J.-H. Tetrahedron. 45:1989;1105.
    • (2002) Modern Organocopper Chemistry , pp. 51-53
    • Knochel, P.1    Betzemeier, B.2    Krause, N.3
  • 18
    • 84993889879 scopus 로고
    • For a review, see: (a) Knochel P., Betzemeier B. Krause N. Modern organocopper chemistry. 2002;51-53 Wiley-VCH, Weinheim. see also: (b) Miyaura N., Itoh M., Suzuki A. Synthesis. 1976;618 (c) Brown H.C., Campbell J.B. Jr. J. Org. Chem. 45:1980;550 (d) Yatagai H. J. Org. Chem. 45:1980;1640 (e) Hoshi M., Masuda Y., Arase A. Bull. Chem. Soc. Jpn. 59:1986;659 (f) Wang K.K., Chu K.-H., Lin Y., Chen J.-H. Tetrahedron. 45:1989;1105.
    • (1976) Synthesis , pp. 618
    • Miyaura, N.1    Itoh, M.2    Suzuki, A.3
  • 19
    • 0006984204 scopus 로고
    • For a review, see: (a) Knochel P., Betzemeier B. Krause N. Modern organocopper chemistry. 2002;51-53 Wiley-VCH, Weinheim. see also: (b) Miyaura N., Itoh M., Suzuki A. Synthesis. 1976;618 (c) Brown H.C., Campbell J.B. Jr. J. Org. Chem. 45:1980;550 (d) Yatagai H. J. Org. Chem. 45:1980;1640 (e) Hoshi M., Masuda Y., Arase A. Bull. Chem. Soc. Jpn. 59:1986;659 (f) Wang K.K., Chu K.-H., Lin Y., Chen J.-H. Tetrahedron. 45:1989;1105.
    • (1980) J. Org. Chem. , vol.45 , pp. 550
    • Brown, H.C.1    Campbell Jr., J.B.2
  • 20
    • 0000126488 scopus 로고
    • For a review, see: (a) Knochel P., Betzemeier B. Krause N. Modern organocopper chemistry. 2002;51-53 Wiley-VCH, Weinheim. see also: (b) Miyaura N., Itoh M., Suzuki A. Synthesis. 1976;618 (c) Brown H.C., Campbell J.B. Jr. J. Org. Chem. 45:1980;550 (d) Yatagai H. J. Org. Chem. 45:1980;1640 (e) Hoshi M., Masuda Y., Arase A. Bull. Chem. Soc. Jpn. 59:1986;659 (f) Wang K.K., Chu K.-H., Lin Y., Chen J.-H. Tetrahedron. 45:1989;1105.
    • (1980) J. Org. Chem. , vol.45 , pp. 1640
    • Yatagai, H.1
  • 21
    • 0003033747 scopus 로고
    • For a review, see: (a) Knochel P., Betzemeier B. Krause N. Modern organocopper chemistry. 2002;51-53 Wiley-VCH, Weinheim. see also: (b) Miyaura N., Itoh M., Suzuki A. Synthesis. 1976;618 (c) Brown H.C., Campbell J.B. Jr. J. Org. Chem. 45:1980;550 (d) Yatagai H. J. Org. Chem. 45:1980;1640 (e) Hoshi M., Masuda Y., Arase A. Bull. Chem. Soc. Jpn. 59:1986;659 (f) Wang K.K., Chu K.-H., Lin Y., Chen J.-H. Tetrahedron. 45:1989;1105.
    • (1986) Bull. Chem. Soc. Jpn , vol.59 , pp. 659
    • Hoshi, M.1    Masuda, Y.2    Arase, A.3
  • 22
    • 0003015989 scopus 로고
    • For a review, see: (a) Knochel P., Betzemeier B. Krause N. Modern organocopper chemistry. 2002;51-53 Wiley-VCH, Weinheim. see also: (b) Miyaura N., Itoh M., Suzuki A. Synthesis. 1976;618 (c) Brown H.C., Campbell J.B. Jr. J. Org. Chem. 45:1980;550 (d) Yatagai H. J. Org. Chem. 45:1980;1640 (e) Hoshi M., Masuda Y., Arase A. Bull. Chem. Soc. Jpn. 59:1986;659 (f) Wang K.K., Chu K.-H., Lin Y., Chen J.-H. Tetrahedron. 45:1989;1105.
    • (1989) Tetrahedron , vol.45 , pp. 1105
    • Wang, K.K.1    Chu, K.-H.2    Lin, Y.3    Chen, J.-H.4
  • 23
    • 85030919988 scopus 로고    scopus 로고
    • note
    • In a similar context it was suggested that syn elimination took place at the level of the vinylcopper intermediate: see Ref. 9f.
  • 28
    • 1542794576 scopus 로고
    • (b) selective oxidation of these vinyl sulfides into vinyl sulfoxides or vinyl sulfones has been carried out successfully by means of dimethyldioxirane: Lévai, A.; Hevesi, L.; Gerard, J. Results to be published. See for example: (a)
    • See for example: (a) De Lucchi O., Pasquato L. Tetrahedron. 44:1988;6755-6794 (b) selective oxidation of these vinyl sulfides into vinyl sulfoxides or vinyl sulfones has been carried out successfully by means of dimethyldioxirane: Lévai, A.; Hevesi, L.; Gerard, J. Results to be published.
    • (1988) Tetrahedron , vol.44 , pp. 6755-6794
    • De Lucchi, O.1    Pasquato, L.2
  • 31
    • 0003624033 scopus 로고
    • A.R. Katritzky, O. Meth-Cohn, & C.W. Rees. London: Academic
    • Heck R.F. Katritzky A.R., Meth-Cohn O., Rees C.W. Palladium reagents in organic syntheses. 1985;2-3 Academic, London.
    • (1985) Palladium Reagents in Organic Syntheses , pp. 2-3
    • Heck, R.F.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.