메뉴 건너뛰기




Volumn 9, Issue 21, 2007, Pages 4227-4230

Palladium(II)-catalyzed annulation of alkynes with ortho-ester-containing phenylboronic acids

Author keywords

[No Author keywords available]

Indexed keywords

ALKYNE; BENZENEBORONIC ACID; BORONIC ACID DERIVATIVE; ESTER; INDENE DERIVATIVE; NAPHTHOL DERIVATIVE; PALLADIUM;

EID: 35548969915     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol701776m     Document Type: Article
Times cited : (113)

References (62)
  • 16
    • 30344443388 scopus 로고    scopus 로고
    • Beletskaya, I. P.; Kashin, A. N.; Litvinov, A. E.; Tyurin, V. S.; Valetsky, P. M.; van Koten, G. Organometallics 2006, 25, 154-158. See also ref 2a.
    • (c) Beletskaya, I. P.; Kashin, A. N.; Litvinov, A. E.; Tyurin, V. S.; Valetsky, P. M.; van Koten, G. Organometallics 2006, 25, 154-158. See also ref 2a.
  • 17
    • 0041660637 scopus 로고    scopus 로고
    • Pd(II)-catalyzed organic transformations using arylboron reagents are as follows but are fewer than Rh(I)-catalyzed ones. 1,4-Addition to α,β-unsaturated carbonyls: (a) Ohe, T.; Uemura, S. Bull. Chem. Soc. Jpn. 2003, 76, 1423-1431.
    • Pd(II)-catalyzed organic transformations using arylboron reagents are as follows but are fewer than Rh(I)-catalyzed ones. 1,4-Addition to α,β-unsaturated carbonyls: (a) Ohe, T.; Uemura, S. Bull. Chem. Soc. Jpn. 2003, 76, 1423-1431.
  • 27
    • 33846615881 scopus 로고    scopus 로고
    • Addition to aldehydes and ketones
    • (k) He, P.; Lu, Y.; Dong, C.-G.; Hu, Q.-S. Org. Lett. 2007, 9, 343-346. 1,2-Addition to aldehydes and ketones:
    • (2007) Org. Lett , vol.9
    • He, P.1    Lu, Y.2    Dong, C.-G.3    Hu, Q.-S.4
  • 31
    • 34249792945 scopus 로고    scopus 로고
    • Qin, C.; Wu, H.; Cheng, J.; Chen, X.; Liu, M.; Zhang, W.; Su, W.; Ding, J. J. Org. Chem. 2007, 72, 4102-4107. See also ref 6k. 1,2-Addition to nitriles:
    • (o) Qin, C.; Wu, H.; Cheng, J.; Chen, X.; Liu, M.; Zhang, W.; Su, W.; Ding, J. J. Org. Chem. 2007, 72, 4102-4107. See also ref 6k. 1,2-Addition to nitriles:
  • 35
    • 33846157728 scopus 로고    scopus 로고
    • (s) Zhao, B.; Lu, X. Org. Lett. 2006, 8, 5987-5990.
    • (2006) Org. Lett , vol.8 , pp. 5987-5990
    • Zhao, B.1    Lu, X.2
  • 43
    • 11844251240 scopus 로고    scopus 로고
    • 8 However, there are a few reports on 1,2-addition of alkyl- or arylrhodium(I) intermediates to the intramolecular ester group, (a) Shintani, R.; Okamoto, K.; Otomaru, Y.; Ueyama, K.; Hayashi, T. J. Am. Chem. Soc. 2005, 127, 54-55.
    • 8 However, there are a few reports on 1,2-addition of alkyl- or arylrhodium(I) intermediates to the intramolecular ester group, (a) Shintani, R.; Okamoto, K.; Otomaru, Y.; Ueyama, K.; Hayashi, T. J. Am. Chem. Soc. 2005, 127, 54-55.
  • 48
    • 34547194244 scopus 로고    scopus 로고
    • Unpublished result. The details will be published as a full paper. During our manuscript preparation, a related reaction was reported by Lu. Song, J.; Shen, Q.; Xu, F.; Lu, X. Org. Lett. 2007, 9, 2947-2950.
    • Unpublished result. The details will be published as a full paper. During our manuscript preparation, a related reaction was reported by Lu. Song, J.; Shen, Q.; Xu, F.; Lu, X. Org. Lett. 2007, 9, 2947-2950.
  • 49
    • 21644463075 scopus 로고    scopus 로고
    • The initial step would involve oxidative addition of 2a to Pd(O) to generate arylpalladium(II) species, (a) Ohe, T.; Ohe, K.; Uemura, S.; Sugita, N. J. Organomet. Chem. 1988, 344, C5-C7.
    • The initial step would involve oxidative addition of 2a to Pd(O) to generate arylpalladium(II) species, (a) Ohe, T.; Ohe, K.; Uemura, S.; Sugita, N. J. Organomet. Chem. 1988, 344, C5-C7.
  • 55
    • 35549006193 scopus 로고    scopus 로고
    • 2-catalyzed annulation of 3d with 2a in MeOH gave 7d in 18% yield, which is better than the yield reported in ref 8a.
    • 2-catalyzed annulation of 3d with 2a in MeOH gave 7d in 18% yield, which is better than the yield reported in ref 8a.
  • 56
    • 17244369977 scopus 로고    scopus 로고
    • (a) Brunel, J. M. Chem. Rev. 2005, 105, 857-897.
    • (2005) Chem. Rev , vol.105 , pp. 857-897
    • Brunel, J.M.1
  • 60
    • 0011404901 scopus 로고    scopus 로고
    • 5 in the presence of an excess of phosphines. Otsuka, S.; Yoshida, T.; Matsumoto, M.; Nakatsu, K. J. Am. Chem. Soc. 1976, 98, 5850-5858.
    • 5 in the presence of an excess of phosphines. Otsuka, S.; Yoshida, T.; Matsumoto, M.; Nakatsu, K. J. Am. Chem. Soc. 1976, 98, 5850-5858.
  • 62
    • 35548949216 scopus 로고    scopus 로고
    • 3 or a reductant such as Zn resulted in similar or lower conversion of 3a. Furthermore, Pd(II) catalysts 10a-d turned out to be less effective than the Pd(O) catalyst and must not be reduced under the reaction conditions.
    • 3 or a reductant such as Zn resulted in similar or lower conversion of 3a. Furthermore, Pd(II) catalysts 10a-d turned out to be less effective than the Pd(O) catalyst and must not be reduced under the reaction conditions.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.