Download PDF
Synthesis 2013; 45(16): 2241-2244
DOI: 10.1055/s-0033-1338909
paper
© Georg Thieme Verlag Stuttgart · New York

Palladium-Catalyzed Reaction of Arylboronic Acids with Aliphatic Nitriles: Synthesis of Alkyl Aryl Ketones and 2-Arylbenzofurans

Xingyong Wang
a   College of Chemistry and Materials Engineering, Wenzhou University, Wenzhou, 3250235, P. R. of China   Fax: +86(577)88368280   Email: jiuxichen@wzu.edu.cn   Email: mcl@wzu.edu.cn
,
Xiaodong Wang
a   College of Chemistry and Materials Engineering, Wenzhou University, Wenzhou, 3250235, P. R. of China   Fax: +86(577)88368280   Email: jiuxichen@wzu.edu.cn   Email: mcl@wzu.edu.cn
,
Miaochang Liu*
a   College of Chemistry and Materials Engineering, Wenzhou University, Wenzhou, 3250235, P. R. of China   Fax: +86(577)88368280   Email: jiuxichen@wzu.edu.cn   Email: mcl@wzu.edu.cn
,
Jinchang Ding
a   College of Chemistry and Materials Engineering, Wenzhou University, Wenzhou, 3250235, P. R. of China   Fax: +86(577)88368280   Email: jiuxichen@wzu.edu.cn   Email: mcl@wzu.edu.cn
b   Wenzhou Vocational and Technical College, Wenzhou, 325035, P. R. of China
,
Jiuxi Chen*
a   College of Chemistry and Materials Engineering, Wenzhou University, Wenzhou, 3250235, P. R. of China   Fax: +86(577)88368280   Email: jiuxichen@wzu.edu.cn   Email: mcl@wzu.edu.cn
,
Huayue Wu
a   College of Chemistry and Materials Engineering, Wenzhou University, Wenzhou, 3250235, P. R. of China   Fax: +86(577)88368280   Email: jiuxichen@wzu.edu.cn   Email: mcl@wzu.edu.cn
› Author Affiliations
Further Information

Publication History

Received: 31 March 2013

Accepted after revision: 29 April 2013

Publication Date:
11 June 2013 (online)

    Permissions and Reprints All articles of this category


Abstract

An efficient palladium-catalyzed addition of arylboronic acids to aliphatic nitriles has been developed, providing a wide range of alkyl aryl ketones in moderate to excellent yields. It is noteworthy that sequential addition and intramolecular annulation reaction of 2-(2-hydroxyphenyl)acetonitriles with arylboronic acids are also conducted smoothly to afford 2-arylbenzofurans in good yields under the standard conditions.

Key words

palladium - aliphatic nitriles - arylboronic acids - alkyl aryl ketones - 2-arylbenzofurans

Supporting Information

    for this article is available online at http://www.thieme-connect.com/ejournals/toc/synthesis.
  • Supporting Information
 

  • References

    • 1a Fleming FF, Wang Q. Chem. Rev. 2003; 103: 2035
      Crossref
    • 1b Kukushkin VY, Pombeiro AJ. L. Chem. Rev. 2002; 102: 1771
      Crossref
    • 2a Ueura K, Miyamura S, Satoh T, Miura M. J. Organomet. Chem. 2006; 691: 2821
      Crossref
    • 2b Shimizu H, Murakami M. Chem. Commun. 2007; 2855
    • 2c Tsui GC, Glenadel Q, Lau C, Lautens M. Org. Lett. 2011; 13: 208
      CrossrefPubMed
  • 4 Wong YC, Parthasarathy K, Cheng CH. Org. Lett. 2010; 12: 1736
    Crossref
    • 5a Culkin DA, Hartwig JF. Acc. Chem. Res. 2003; 36: 234
      Crossref
    • 5b Culkin DA, Hartwig JF. J. Am. Chem. Soc. 2002; 124: 9330
      Crossref
    • 6a Jie S, Zhang S, Sun WH. Eur. J. Inorg. Chem. 2007; 5584
    • 6b Ball SC, Davies RP, Raithby PR, Shields GP, Snaith R. J. Organomet. Chem. 1998; 550: 457
      Crossref
    • 6c Clegg W, Davies RP, Dunbar L, Feeder N, Liddle ST, Mulvey RE, Snaith R, Wheatley AE. H. Chem. Commun. 1999; 1401
  • 7 Malamas MS, Erdei J, Gunawan I, Barnes K, Johnson M, Hui Y, Turner J, Hu Y, Wagner E, Fan K, Olland A, Bard J, Robichaud AJ. J. Med. Chem. 2009; 52: 6314
    Crossref
    • 8a Suzuki A. Acc. Chem. Res. 1982; 15: 178
      Crossref
    • 8b Miyaura N, Suzuki A. Chem. Rev. 1995; 95: 2457
    • 8c Suzuki A. J. Organomet. Chem. 1998; 576: 147
    • 9a Chen J, Peng Y, Liu M, Ding J, Su W, Wu H. Adv. Synth. Catal. 2012; 354: 2117
      Crossref
    • 9b Zhang J, Chen J, Liu M, Zheng X, Ding J, Wu H. Green Chem. 2012; 14: 912
      Crossref
    • 9c Lu W, Chen J, Liu M, Ding J, Gao W, Wu H. Org. Lett. 2011; 13: 6114
      Crossref
    • 9d Zheng X, Ding J, Chen J, Gao W, Liu M, Wu H. Org. Lett. 2011; 13: 1726
      Crossref
    • 9e Zheng H, Zhang Q, Chen J, Liu M, Cheng S, Ding J, Wu H, Su W. J. Org. Chem. 2009; 74: 943
      Crossref
    • 9f Qin C, Wu H, Chen J, Liu M, Cheng J, Su W, Ding J. Org. Lett. 2008; 10: 1537
    • 9g Qin C, Wu H, Cheng J, Chen X, Liu M, Zhang W, Su W, Ding J. J. Org. Chem. 2007; 72: 4102
      Crossref
    • 10a Jia C, Piao D, Oyamada J, Lu W, Kitamura T, Fujiwara Y. Science 2000; 287: 1992
    • 10b Jia C, Lu W, Oyamada J, Kitamura T, Matsuda K, Irie M, Fujiwara Y. J. Am. Chem. Soc. 2000; 122: 7252
      Crossref
    • 10c Jia C, Kitamura T, Fujiwara Y. Acc. Chem. Res. 2001; 34: 633
      CrossrefPubMed
    • 11a Horton DA, Bourne GT, Smythe ML. Chem. Rev. 2003; 103: 893
      CrossrefPubMed
    • 11b Jiang X, Liu W, Zhang W, Jiang F, Gao Z, Zhuang H, Fu L. Eur. J. Med. Chem. 2011; 46: 3526
      Crossref
    • 11c Moussa IA, Banister SD, Beinat C, Giboureau N, Reynolds A, Kassoiu M. J. Med. Chem. 2010; 53: 6228
      Crossref