Download PDF
Synlett 2020; 31(09): 829-837
DOI: 10.1055/s-0039-1690779
synpacts
© Georg Thieme Verlag Stuttgart · New York

Epoxides as Dual-Functionalized Alkylating Reagents in Catellani Reactions for the Assembly of Heterocycles

Chenggui Wu
a   Sauvage Center for Molecular Sciences, Engineering Research Center of Organosilicon Compounds and Materials (Ministry of Education), College of Chemistry and Molecular Sciences, Wuhan University, 430072 Wuhan, P. R. of China   Email: hgcheng@whu.edu.cn
,
Hong-Gang Cheng∗
a   Sauvage Center for Molecular Sciences, Engineering Research Center of Organosilicon Compounds and Materials (Ministry of Education), College of Chemistry and Molecular Sciences, Wuhan University, 430072 Wuhan, P. R. of China   Email: hgcheng@whu.edu.cn
,
Qianghui Zhou∗
a   Sauvage Center for Molecular Sciences, Engineering Research Center of Organosilicon Compounds and Materials (Ministry of Education), College of Chemistry and Molecular Sciences, Wuhan University, 430072 Wuhan, P. R. of China   Email: hgcheng@whu.edu.cn
b   The Institute for Advanced Studies, Wuhan University, 430072 Wuhan, P. R. of China   Email: qhzhou@whu.edu.cn
› Author AffiliationsWe are grateful to the National 1000-Youth Talents Plan, the Innovation Team Program of Wuhan University (Program No. 2042017kf0232), start-up funding from Wuhan University, National Natural Science Foundation of China (Grants 21871213, and 21801193), and the China Postdoctoral Science Foundation (No. 2016M602339, H.G.C.) for financial support.
Further Information

Publication History

Received: 05 November 2019

Accepted after revision: 05 December 2019

Publication Date:
02 January 2020 (online)

    Permissions and Reprints All articles of this category


Abstract

Reported is a cooperative catalytic system consisting of a complex of Pd with dicyclohexyl(2′,4′,6′-triisopropylbiphenyl-2-yl)phosphine (XPhos) and the potassium salt of 5-norbornene-2-carboxylic acid that permits the use of epoxides as dual-functionalized alkylating reagents in Catellani-type reactions for the assembly of heterocycles. Salient features of this research include readily available substrates, use of the potassium salt of 5-norbornene-2-carboxylic acid as a catalytic mediator as well as a base, and excellent regioselectivity for the cleavage of epoxides. This mild, chemoselective, scalable, atom- and step-economic protocol offers a straightforward approach for the assembly of isochroman and 2,3-dihydrobenzofuran scaffolds.

Key words

Catellani reaction - cooperative catalysis - epoxides - isochromans - dihydrobenzofurans
 

  • References and Notes

  • 1 For seminal work, see: Catellani M, Frignani F, Rangoni A. Angew. Chem. Int. Ed. 1997; 36: 119
    Crossref

      • For related reviews, see:
    • 2a Catellani M. Top. Organomet. Chem. 2005; 14: 21
    • 2b Lautens M, Alberico D, Bressy C, Fang Y.-Q, Mariampillai B, Wilhelm T. Pure Appl. Chem. 2006; 78: 351
      Crossref
    • 2c Catellani M, Motti E, Della Ca’ N. Acc. Chem. Res. 2008; 41: 1512
      CrossrefPubMed
    • 2d Martins A, Mariampillai B, Lautens M. Top. Curr. Chem. 2010; 292: 1
      PubMed
    • 2e Ferraccioli R. Synthesis 2013; 45: 581
      Article in Thieme Connect
    • 2f Ye J, Lautens M. Nat. Chem. 2015; 7: 863
      CrossrefPubMed
    • 2g Zhu H, Ye C, Chen Z. Youji Huaxue 2015; 35: 2291
    • 2h Della Ca’ N, Fontana M, Motti E, Catellani M. Acc. Chem. Res. 2016; 49: 1389
      CrossrefPubMed
    • 2i Kim D.-S, Park W.-J, Jun C.-H. Chem. Rev. 2017; 117: 8977
      CrossrefPubMed
    • 2j Zhao K, Ding L, Gu Z. Synlett 2018; 29: 129
    • 2k Cheng H.-G, Chen S, Chen R, Zhou Q. Angew. Chem. Int. Ed. 2019; 58: 5832
      CrossrefPubMed
    • 2l Wang J, Dong G. Chem. Rev. 2019; 119: 7478
      CrossrefPubMed

      For mechanistic studies on Catellani-type reactions, see:
    • 3a Catellani M, Cugini F, Bocelli G. J. Organomet. Chem. 1999; 584: 63
      Crossref
    • 3b Cárdenas DJ, Martín-Matute B, Echavarren AM. J. Am. Chem. Soc. 2006; 128: 5033
      CrossrefPubMed
    • 3c Larraufie M.-H, Maestri G, Beaume É, Derat P, Ollivier C, Fensterbank L, Courillon C, Lacôte E, Catellani M, Malacria M. Angew. Chem. Int. Ed. 2011; 50: 12253
      CrossrefPubMed
    • 3d Maestri G, Motti E, Della Ca’ N, Malacria M, Derat E, Catellani M. J. Am. Chem. Soc. 2011; 133: 8574
      CrossrefPubMed
    • 3e Chai DI, Thansandote P, Lautens M. Chem. Eur. J. 2011; 17: 8175
      CrossrefPubMed
  • 4 For the first example of an alkyl halide as an electrophile, see ref. 2.
  • 5 For the first example of aryl halide as an electrophile, see: Catellani M, Motti E, Baratta S. Org. Lett. 2001; 3: 3611
    CrossrefPubMed
    • 6a Candito DA, Lautens M. Org. Lett. 2010; 12: 3312
      CrossrefPubMed
    • 6b Liu C, Liang Y, Zhang N, Zhang BS, Feng Y, Bi S, Liang Y.-M. Chem. Commun. 2018; 54: 3407
      CrossrefPubMed
    • 6c Qian G, Bai M, Gao S, Chen H, Zhou S, Cheng H.-G, Yan W, Zhou Q. Angew. Chem. Int. Ed. 2018; 57: 10984

      For selected examples, see:
    • 7a Dong Z, Dong G. J. Am. Chem. Soc. 2013; 135: 18350
      CrossrefPubMed
    • 7b Chen Z.-Y, Ye C.-Q, Zhu H, Zeng X.-P, Yuan J.-J. Chem. Eur. J. 2014; 20: 4237
      CrossrefPubMed
    • 7c Zhou P.-X, Ye Y.-Y, Ma J.-W, Zheng L, Tang Q, Qiu Y.-F, Song B, Qiu Z.-H, Xu P.-F, Liang Y.-M. J. Org. Chem. 2014; 79: 6627
      CrossrefPubMed
    • 7d Pan S, Ma X, Zhong D, Chen W, Liu M, Wu H. Adv. Synth. Catal. 2015; 357: 3052
      Crossref
    • 7e Shi H, Babinski DJ, Ritter T. J. Am. Chem. Soc. 2015; 137: 3775
      CrossrefPubMed
    • 7f Sun F, Gu Z. Org. Lett. 2015; 17: 2222
      CrossrefPubMed
    • 7g Wang P, Li G.-C, Jain P, Farmer ME, He J, Shen P.-X, Yu J.-Q. J. Am. Chem. Soc. 2016; 138: 14092
      CrossrefPubMed
    • 7h Fu WC, Zheng B, Zhao Q, Chan WT. K, Kwong FY. Org. Lett. 2017; 19: 4335
      CrossrefPubMed
    • 7i Whyte A, Olson ME, Lautens M. Org. Lett. 2018; 20: 345
      CrossrefPubMed

      For selected examples, see:
    • 8a Zhou P.-X, Ye Y.-Y, Liu C, Zhao L.-B, Hou J.-Y, Chen D.-Q, Tang Q, Wang A.-Q, Zhang J.-Y, Huang Q.-X, Xu P.-F, Liang Y.-M. ACS Catal. 2015; 5: 4927
      Crossref
    • 8b Dong Z, Wang J, Ren Z, Dong G. Angew. Chem. Int. Ed. 2015; 54: 12664
      CrossrefPubMed
    • 8c Huang Y, Zhu R, Zhao K, Gu Z. Angew. Chem. Int. Ed. 2015; 54: 12669
      CrossrefPubMed
    • 8d Pan S, Wu F, Yu R, Chen W. J. Org. Chem. 2016; 81: 1558
      CrossrefPubMed
    • 8e Sun F, Li M, He C, Wang B, Li B, Sui X, Gu Z. J. Am. Chem. Soc. 2016; 138: 7456
      CrossrefPubMed
    • 8f Wang J, Zhang L, Dong Z, Dong G. Chem 2016; 1: 581
    • 8g Xu S, Jiang J, Ding L, Fu Y, Gu Z. Org. Lett. 2018; 20: 325
      CrossrefPubMed
    • 8h Fan X, Gu Z. Org. Lett. 2018; 20: 1187
      CrossrefPubMed
    • 10a Wang Z, Kuninobu Y, Kanai M. J. Am. Chem. Soc. 2015; 137: 6140
      CrossrefPubMed
    • 10b Cheng G, Li T, Yu J.-Q. J. Am. Chem. Soc. 2015; 137: 10950
      CrossrefPubMed
    • 10c Li D.-D, Niu L.-F, Ju Z.-Y, Xu Z, Wu C. Eur. J. Org. Chem. 2016; 3090

      For selected reviews, see:
    • 11a Nising CF, Bräse S. Chem. Soc. Rev. 2008; 37: 1218
      CrossrefPubMed
    • 11b Hu J, Bian M, Ding H. Tetrahedron Lett. 2016; 57: 5519
      Crossref
    • 12a Palucki M, Wolfe J, Buchwald S. J. Am. Chem. Soc. 1996; 118: 10333
      Crossref
    • 12b Mann G, Hartwig J. J. Am. Chem. Soc. 1996; 118: 13109
      Crossref

      For recent reviews, see:
    • 13a Bertolini F, Pineschi M. Org. Prep. Proced. Int. 2009; 41: 385
      Crossref
    • 13b Sheppard TD. J. Chem. Res. 2011; 35: 377
      Crossref
  • 15 Cheng H.-G, Wu C, Chen H, Chen R, Qian G, Geng Z, Wei Q, Xia Y, Zhang J, Zhang Y, Zhou Q. Angew. Chem. Int. Ed. 2018; 57: 3444
    CrossrefPubMed
    • 16a Lautens M, Piguel S. Angew. Chem. Int. Ed. 2000; 39: 1045
      CrossrefPubMed
    • 16b Huang X, Anderson KW, Zim D, Jiang L, Klapars A, Buchwald SL. J. Am. Chem. Soc. 2003; 125: 6653
      CrossrefPubMed
  • 17 CCDC 1816726 and 1816908 contains the supplementary crystallographic data for compounds 4e' and 5e′′, respectively. The data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/getstructures.
  • 18 Wu C, Cheng H.-G, Chen R, Chen H, Liu Z.-S, Zhang J, Zhang Y, Zhu Y, Geng Z, Zhou Q. Org. Chem. Front. 2018; 5: 2533
    Crossref
  • 19 Richter H, Rohlmann R, Mancheño OG. Chem. Eur. J. 2011; 17: 11622
    CrossrefPubMed
  • 20 TenBrink RE, Bergh CL, Duncan JN, Harris DW, Huff RM, Lahti RA, Lawson CF, Lutzke BS, Martin IJ, Rees SA, Schlachter SK, Sih JC, Smith MW. J. Med. Chem. 1996; 39: 2435
    CrossrefPubMed
  • 21 Allen JC, Kociok-Köhn G, Frost CG. Org. Biomol. Chem. 2012; 10: 32
    CrossrefPubMed
  • 22 Chen L, Liu W, Huang K, Hu X, Fang Z.-X, Wu J.-L, Zhang Q.-Q. Heterocycles 2011; 83: 1853
    Crossref
    • 23a Rozenzweig-Lipson S, Brandt MR. WO 2006/116171, 2006
    • 23b Rosenzweig-Lipson S. US 20070225334, 2007
    • 23c Gross JL, Williams MJ, Stack GP, Gao H, Zhou D. US 2005143452, 2008 ; Chem. Abstr. 2008, 149, 471316
  • 24 Gontcharov AV, Shaw C.-C, Yu Q, Tadayon S, Bernatchez M, Lankau M, Cantin M, Potoski JR, Khafizova G, Stack G, Gross J, Zhou D. Org. Process Res. Dev. 2010; 14: 1438
    Crossref
  • 25 Wu C, Yang X, Shang Y, Cheng H.-G, Yan W, Zhou Q. Org. Lett. 2019; 21: 8938
    CrossrefPubMed
  • 26 Lei C, Jin X, Zhou J. Angew. Chem. Int. Ed. 2015; 54: 13397
    CrossrefPubMed