Synlett 2018; 29(19): 2547-2551
DOI: 10.1055/s-0037-1610261
cluster
© Georg Thieme Verlag Stuttgart · New York

Iterative Synthesis of Edge-Bent [3]Naphthylene

Zexin Jin
a   Department of Chemistry, Stanford University, Stanford, California 94305, United States   eMail: yanx@stanford.edu
,
Yew Chin Teo
a   Department of Chemistry, Stanford University, Stanford, California 94305, United States   eMail: yanx@stanford.edu
,
Simon J. Teat
b   Advanced Light Source, Lawrence Berkeley National Laboratory, Berkeley, California 94720, United States
,
Yan Xia  *
a   Department of Chemistry, Stanford University, Stanford, California 94305, United States   eMail: yanx@stanford.edu
› Institutsangaben
This work was supported by a Cottrell Scholar Award (24067) from the Research Corporation for Science Advancement.
Weitere Informationen

Publikationsverlauf

Received: 22. Juni 2018

Accepted after revision: 15. Juli 2018

Publikationsdatum:
28. August 2018 (online)


Published as part of the Cluster Synthesis of Materials

Abstract

Polycyclic conjugated hydrocarbons (PCHs) containing antiaromatic rings are of fundamental and technical interest. [N]naphthylene is an intriguing family of PCHs consisting of alternatingly fused naphthalenoids and antiaromatic cyclobutadienoids (CBDs). We recently reported the first three regioisomers of the [N]naphthylene family, synthesized by catalytic arene-norbornene annulation (CANAL) reaction followed by acidic aromatization. We now report an iterative strategy for CANAL synthesis allowing us to synthesize the forth regioisomer, edge-bent [3]naphthylene. The optoelectronic properties, local paratropicity, and crystal packing of the edge-bent [3]naphthylene were studied and compared with its closely related regioisomer, center-bent [3]naphthylene.

Supporting Information

 
  • References and Notes

    • 1a Ronald B. Frank WF. Jr. J. Phys.: Condens. Matter 2008; 20: 374104
    • 1b Kawase T. Konishi A. Hirao Y. Matsumoto K. Kurata H. Kubo T. Chem. Eur. J. 2009; 15: 2653
    • 1c Levi ZU. Tilley TD. J. Am. Chem. Soc. 2009; 131: 2796
    • 1d Chase DT. Rose BD. McClintock SP. Zakharov LN. Haley MM. Angew. Chem. Int. Ed. 2011; 50: 1127
    • 1e Iida A. Yamaguchi S. J. Am. Chem. Soc. 2011; 133: 6952
    • 1f Nishinaga T. Ohmae T. Aita K. Takase M. Iyoda M. Arai T. Kunugi Y. Chem. Commun. 2013; 49: 5354
    • 1g Shimizu A. Kishi R. Nakano M. Shiomi D. Sato K. Takui T. Hisaki I. Miyata M. Tobe Y. Angew. Chem. Int. Ed. 2013; 52: 6076
    • 1h Zhao J. Oniwa K. Asao N. Yamamoto Y. Jin T. J. Am. Chem. Soc. 2013; 135: 10222
    • 1i Fix AG. Chase DT. Haley MM. Top. Curr. Chem. 2014; 349: 159
    • 1j Parkhurst R. Swager T. Top. Curr. Chem. 2014; 350: 141
    • 1k Rosenberg M. Dahlstrand C. Kilså K. Ottosson H. Chem. Rev. 2014; 114: 5379
    • 1l Cao J. London G. Dumele O. von Wantoch Rekowski M. Trapp N. Ruhlmann L. Boudon C. Stanger A. Diederich F. J. Am. Chem. Soc. 2015; 137: 7178
    • 1m Furuyama T. Sato T. Kobayashi N. J. Am. Chem. Soc. 2015; 137: 13788
    • 1n Frederickson CK. Zakharov LN. Haley MM. J. Am. Chem. Soc. 2016; 138: 16827
    • 2a Anthony JE. Chem. Rev. 2006; 106: 5028
    • 2b Anthony JE. Angew. Chem. Int. Ed. 2008; 47: 452
    • 2c Kawase T. Fujiwara T. Kitamura C. Konishi A. Hirao Y. Matsumoto K. Kurata H. Kubo T. Shinamura S. Mori H. Miyazaki E. Takimiya K. Angew. Chem. Int. Ed. 2010; 49: 7728
    • 2d Mei J. Diao Y. Appleton AL. Fang L. Bao Z. J. Am. Chem. Soc. 2013; 135: 6724
    • 3a Breslow R. Schneebeli ST. Tetrahedron 2011; 67: 10171
    • 3b Chen W. Li H. Widawsky JR. Appayee C. Venkataraman L. Breslow R. J. Am. Chem. Soc. 2014; 136: 918
    • 3c Fujii S. Marqués-González S. Shin J.-Y. Shinokubo H. Masuda T. Nishino T. Arasu NP. Vázquez H. Kiguchi M. Nat. Commun. 2017; 8: 15984
    • 3d Yin X. Zang Y. Zhu L. Low JZ. Liu Z.-F. Cui J. Neaton JB. Venkataraman L. Campos LM. Sci. Adv. 2017; 3: eaao2615
  • 4 Narita A. Wang X.-Y. Feng X. Mullen K. Chem. Soc. Rev. 2015; 44: 6616
  • 5 Bally T. Masamune S. Tetrahedron 1980; 36: 343
    • 6a Biegger P. Schaffroth M. Patze C. Tverskoy O. Rominger F. Bunz UH. F. Chem. Eur. J. 2015; 21: 7048
    • 6b Yang S. Shan B. Xu X. Miao Q. Chem. Eur. J. 2016; 22: 6637
    • 7a Berris BC. Hovakeemian GH. Lai YH. Mestdagh H. Vollhardt KP. C. J. Am. Chem. Soc. 1985; 107: 5670
    • 7b Miljanić OŠ. Vollhardt KP. C. [N]Phenylenes: A Novel Class of Cyclohexatrienoid Hydrocarbons. In Carbon-Rich Compounds: From Molecules to Materials. Wiley-VCH; Weinheim: 2006: 140
    • 8a Humayun Kabir SM. Hasegawa M. Kuwatani Y. Yoshida M. Matsuyama H. Iyoda M. J. Chem. Soc., Perkin Trans. 1 2001; 159
    • 8b Parkhurst RR. Swager TM. J. Am. Chem. Soc. 2012; 134: 15351
    • 8c Florian S. Tomohiko N. Volker E. Klaus M. Angew. Chem. Int. Ed. 2014; 53: 1538
    • 8d Fukazawa A. Oshima H. Shimizu S. Kobayashi N. Yamaguchi S. J. Am. Chem. Soc. 2014; 136: 8738
    • 8e Sheng-Li W. Ming-Lun P. Wei-Siang S. Yao-Ting W. Angew. Chem. Int. Ed. 2017; 56: 14694
    • 9a Jin Z. Teo YC. Teat SJ. Xia Y. J. Am. Chem. Soc. 2017; 139: 15933
    • 9b Jin Z. Teo YC. Zulaybar NG. Smith MD. Xia Y. J. Am. Chem. Soc. 2017; 139: 1806
    • 9c Teo YC. Jin Z. Xia Y. Org. Lett. 2018; 20: 3300
  • 10 Ooi T. Takahashi M. Yamada M. Tayama E. Omoto K. Maruoka K. J. Am. Chem. Soc. 2004; 126: 1150
  • 11 For one example using HBr in Aliquat-336 to cleave a methoxy group, see: Waghmode SB. Mahale G. Patil VP. Renalson K. Singh D. Synth. Commun. 2013; 43: 3272
  • 13 Compound 10 To an oven-dried 15 mL pressure tube was added 8 (56.8 mg, 0.132 mmol), 9 (74.5 mg, 0.14 mmol), palladium acetate (2.9 mg, 0.013 mmol) and Johnphos ligand (7.7 mg, 0.026 mmol). The tube was then transferred to a glovebox, and cesium carbonate (44.0 mg, 0.132 mmol) and THF (1mL) were added. The tube was closed and taken outside glovebox. The mixture was stirred at room temperature for 5 min, and then heated to 130 °C. After 24 h, the reaction was cooled to room temperature, and was passed through a thin layer of Celite to remove the inorganic salt. The solution was concentrated in vacuo and the residue was purified by column chromatography (1:10 EtOAc/hexanes) to yield 10 as a light yellow solid (70.5 mg, 66% yield). 1H NMR (400 MHz, chloroform-d): δ = 7.85 (d, J = 8.4 Hz, 1 H), 7.68 (d, J = 8.3 Hz, 1 H), 7.53 (d, J = 7.9 Hz, 1 H), 7.45 – 7.35 (m, 2 H), 7.34 (s, 1H), 7.33 (s, 2 H), 7.30 (ddd, J = 8.1, 6.7, 1.1 Hz, 1 H), 7.21 (d, J = 7.9 Hz, 1 H), 3.47 (s, 2 H), 2.58 (s, 3 H), 2.36 (s, 3 H), 1.85 (s, 3 H), 1.84 (s, 3 H), 1.17 (s, 42 H) ppm. 13C NMR (101 MHz, chloroform-d): δ = 148.53, 148.21, 147.46, 144.50, 143.83, 140.59, 140.48, 137.17, 137.05, 134.74, 130.03, 129.77, 127.12, 126.36, 125.41, 124.36, 124.28, 123.27, 119.59, 119.48, 118.40, 118.12, 117.81, 105.78, 94.82, 83.87, 55.11, 55.09, 18.80, 16.44, 14.95, 14.22, 11.36 ppm. m/z [M + Na+] calcd for C56H66OSi2: 833.46; found: 833.45.
  • 14 [3]Naphthylene 1 Compound 10 (20.0 mg, 0.022 mmol) was dissolved in isopropyl alcohol (1 mL), chloroform (0.5 mL), and HCl (0.2 ml, 37%). The solution was heated at 80 °C for 24 h. The reaction mixture was cooled, and the aromatized product had crushed out of the solution. The product 1 was collected by filtration and washed with MeOH to give an orange solid (15.8 mg, 82%). 1H NMR (500 MHz, chloroform-d): δ = 7.67 (d, J = 8.4 Hz, 1 H), 7.59 (d, J = 8.3 Hz, 1 H), 7.55 (s, 1 H), 7.54 (s, 1 H), 7.40 (d, J = 7.8 Hz, 1 H), 7.34 (t, J = 7.5 Hz, 1 H), 7.24 (t, J = 7.6 Hz, 1 H), 7.07 (d, J = 7.9 Hz, 1 H), 7.05 (s, 1 H), 7.03 (s, 1 H), 2.46 (s, 3 H), 2.35 (s, 3 H), 2.34 (s, 3 H), 2.28 (s, 3 H), 1.19 (s, 42 H) ppm. 13C NMR (101 MHz, chloroform-d): δ = 148.33, 147.35, 146.34, 146.20, 146.10, 145.52, 145.51, 145.44, 137.73, 137.64, 134.94, 134.92, 134.71, 130.23, 129.76, 129.49, 129.46, 127.13, 125.98, 125.63, 124.02, 121.85, 121.80, 120.23, 120.19, 120.00, 117.19, 114.64, 114.22, 106.66, 93.90, 19.10, 16.55, 15.13, 14.71, 14.64, 11.70 ppm. m/z [M + Na+] calcd for C56H64Si2: 815.44; found: 815.34.