Palladium-catalyzed Cycloaromatization Polymerization of Enediynes

Chonggang Wang; Shudan Chen; Hao Zhou; Jinlou Gu; Aiguo Hu

doi:10.1007/s10118-018-2088-9

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Palladium-catalyzed Cycloaromatization Polymerization of Enediynes

Articles | Updated：2021-02-18

- Palladium-catalyzed Cycloaromatization Polymerization of Enediynes
- Chinese Journal of Polymer Science Vol. 36, Issue 2, Pages: 237-243(2018)
- Affiliations：
  
  Shanghai Key Laboratory of Advanced Polymeric Materials, School of Materials Science and Engineering, East China University of Science and Technology, Shanghai 200237, China
- Author bio：
  
  Aiguo Hu, E-mail hagmhsn@ecust.edu.cn
- Funds：
- DOI：10.1007/s10118-018-2088-9
  CLC：
- Received：29 September 2017，
  
  Accepted：06 November 2017，
  
  Online First：01 December 2017，
  
  Published：05 February 2018
- Accepted：
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Chonggang Wang, Shudan Chen, Hao Zhou, et al. Palladium-catalyzed Cycloaromatization Polymerization of Enediynes[J]. Chinese Journal of Polymer Science, 2018, 36(2): 237-243.
DOI：

Chonggang Wang, Shudan Chen, Hao Zhou, et al. Palladium-catalyzed Cycloaromatization Polymerization of Enediynes[J]. Chinese Journal of Polymer Science, 2018, 36(2): 237-243. DOI： 10.1007/s10118-018-2088-9.

摘要

Abstract

Bergman cyclization has shown great promise in constructing conjugated polymers. However

the application of this reaction in polymer science is still limited due to the harsh reaction condition and ill-defined structure of the achieved polymers. To this end

the cycloaromatization polymerization of enediynes catalyzed by a series of transition metal catalysts is investigated in this work

by taking advantage of the coordination chemistry of the enediyne with the transition metal complexes. According to the nuclear magnetic resonance (NMR)

Fourier transform infrared (FTIR)

ultraviolet-visble (UV-Vis) spectroscopies and matrix-assisted laser desorption/ionization time-offlight mass spectrometry (MALDI-TOF MS) analysis

the cycloaromatization polymerization of enediynes proceeds under milder conditions and in a more controlled manner in the presence of palladium(Ⅱ) complexes

giving structurally regulated conjugated polymers in high yields.

关键词

Keywords

references

I. V. Alabugin , M. Manoharan . Radical-anionic cyclizations of enediynes:remarkable effects of benzannelation and remote substituents on cyclorearomatization reactions . J. Am. Chem. Soc. , 2003 . 125 ( 15 ): 4495 - 4509 . DOI: 10.1021/ja029664u http://doi.org/10.1021/ja029664u .

R. K. Mohamed , P. W. Peterson , I. V. Alabugin . Concerted reactions that produce diradicals and zwitterions:electronic, steric, conformational, and kinetic control of cycloaromatization processes . Chem. Rev. , 2013 . 113 ( 9 ): 7089 - 7129 . DOI: 10.1021/cr4000682 http://doi.org/10.1021/cr4000682 .

Y. Xiao , A. Hu . Bergman cyclization in polymer chemistry and material science . Macromol. Rapid Commun. , 2011 . 32 ( 21 ): 1688 - 1698 . DOI: 10.1002/marc.201100378 http://doi.org/10.1002/marc.201100378 .

S. Chen , A. Hu . Recent advances of the Bergman cyclization in polymer science . Sci. China:Chem. , 2015 . 58 ( 11 ): 1710 - 1723 . DOI: 10.1007/s11426-015-5460-4 http://doi.org/10.1007/s11426-015-5460-4 .

Q. Sun , C. Zhang , Z. Li , H. Kong , Q. Tan , A. Hu , W. Xu . On-surface formation of one-dimensional polyphenylene through Bergman cyclization . J. Am. Chem. Soc. , 2013 . 135 ( 23 ): 8448 - 8451 . DOI: 10.1021/ja404039t http://doi.org/10.1021/ja404039t .

J. B. Biggins , K. C. Onwueme , J. S. Thorson . Resistance to enediyne antitumor antibiotics by calC self-sacrifice . Science , 2003 . 301 ( 5639 ): 1537 - 1541 . DOI: 10.1126/science.1086695 http://doi.org/10.1126/science.1086695 .

S. V. Kovalenko , S. Peabody , M. Manoharan , R. J. Clark , I. V. Alabugin . 5-Exo-dig radical cyclization of enediynes:the first synthesis of tin-substituted benzofulvenes . Org. Lett. , 2004 . 6 ( 14 ): 2457 - 2460 . DOI: 10.1021/ol049122c http://doi.org/10.1021/ol049122c .

P. M. Byers , J. I. Rashid , R. K. Mohamed , I. V. Alabugin . Polyaromatic ribbon/benzofuran fusion via consecutive endo cyclizations of enediynes . Org. Lett. , 2012 . 14 ( 23 ): 6032 - 6035 . DOI: 10.1021/ol302922t http://doi.org/10.1021/ol302922t .

I. V. Alabugin , K. Gilmore , S. Patil , M. Manoharan , S. V. Kovalenko , R. J. Clark , I. Ghiviriga . Radical cascade transformations of tris(o-aryleneethynylenes) into substituted Benzo . J. Am. Chem. Soc. , 2008 . 130 ( 34 ): 11535 - 11545 . DOI: 10.1021/ja8038213 http://doi.org/10.1021/ja8038213 .

C. L. Perrin , B. L. Rodgers , J. M. O'Connor . Nucleophilic addition to ap-benzyne derived from an enediyne:a new mechanism for halide incorporation into biomolecules . J. Am. Chem. Soc. , 2007 . 129 ( 15 ): 4795 - 4799 . DOI: 10.1021/ja070023e http://doi.org/10.1021/ja070023e .

A. V. Gulevskaya , A. S. Tyaglivy . Nucleophilic cyclizations of enediynes as a method for polynuclear heterocycle synthesis . Chem. Heterocycl. Compd. , 2012 . 48 ( 1 ): 82 - 94 . DOI: 10.1007/s10593-012-0972-8 http://doi.org/10.1007/s10593-012-0972-8 .

C. L. Perrin , G. J. Reyes-Rodríguez . Selectivity and isotope effects in hydronation of a naked aryl anion . J. Am. Chem. Soc. , 2014 . 136 ( 43 ): 15263 - 15269 . DOI: 10.1021/ja507517g http://doi.org/10.1021/ja507517g .

A. V. Gulevskaya , R. Y. Lazarevich , A. F. Pozharskii . Electrophilic cyclizations of 2, 3-dialkynylquinoxalines and 1, 2-dialkynylbenzenes:a comparative study . Tetrahedron , 2013 . 69 ( 2 ): 910 - 917 . DOI: 10.1016/j.tet.2012.10.098 http://doi.org/10.1016/j.tet.2012.10.098 .

A. V. Gulevskaya , R. Y. Lazarevich . Cyclizations of enediynes under the action of electrophiles . Chem. Heterocycl. Compd. , 2013 . 49 ( 1 ): 116 - 139 . DOI: 10.1007/s10593-013-1234-0 http://doi.org/10.1007/s10593-013-1234-0 .

S. Chen , Q. Li , S. Sun , Y. Ding , A. Hu . A novel approach toward polyfulvene:cationic polymerization of enediynes . Macromolecules , 2017 . 50 ( 2 ): 534 - 541 . DOI: 10.1021/acs.macromol.6b02321 http://doi.org/10.1021/acs.macromol.6b02321 .

Y. Wang , M. Finn . Organometallic diradical cycloaromatization reaction . J. Am. Chem. Soc. , 1995 . 117 ( 30 ): 8045 - 8046 . DOI: 10.1021/ja00135a035 http://doi.org/10.1021/ja00135a035 .

B. P. Taduri , Y. F. Ran , C. W. Huang , R. S. Liu . Platinum-catalyzed aromatization of enediynes via a C-H bond insertion of tethered alkanes . Org. Lett. , 2006 . 8 ( 5 ): 883 - 886 . DOI: 10.1021/ol052962m http://doi.org/10.1021/ol052962m .

J. M. O'Connor , S. J. Friese , M. Tichenor . Ruthenium-mediated cycloaromatization of acyclic enediynes and dienynes at ambient temperature . J. Am. Chem. Soc. , 2002 . 124 ( 14 ): 3506 - 3507 . DOI: 10.1021/ja017873t http://doi.org/10.1021/ja017873t .

M. H. Larsen , K. N. Houk , A. S. K. Hashmi . Dual gold catalysis:stepwise catalyst transfer via dinuclear clusters . J. Am. Chem. Soc. , 2015 . 137 ( 33 ): 10668 - 10676 . DOI: 10.1021/jacs.5b05773 http://doi.org/10.1021/jacs.5b05773 .

A. Basak , S. Mandal , S. S. Bag . Chelation-controlled Bergman cyclization:synthesis and reactivity of enediynyl ligands . Chem. Rev. , 2003 . 103 ( 10 ): 4077 - 4094 . DOI: 10.1021/cr020069k http://doi.org/10.1021/cr020069k .

J. M. O'Connor , S. J. Friese , B. L. Rodgers . A transition-metal-catalyzed enediyne cycloaromatization . J. Am. Chem. Soc. , 2005 . 127 ( 47 ): 16342 - 16343 . DOI: 10.1021/ja050060a http://doi.org/10.1021/ja050060a .

B. Zhu , G. Qian , Y. Xiao , S. Deng , M. Wang , A. Hu . A convergence of photo-Bergman cyclization and intramolecular chain collapse towards polymeric nanoparticles . J. Polym. Sci., Part A:Polym. Chem. , 2011 . 49 ( 24 ): 5330 - 5338 . DOI: 10.1002/pola.v49.24 http://doi.org/10.1002/pola.v49.24 .

T. Manabe , S.-i. Yanagi , K. Ohe , S. Uemura . New examples of 1, 6-and 1, 7-hydrogen transfer promoted by an α-silyl group in Rhodium(Ⅰ)-catalyzed radical reactions of acyclic enediynes . Organometallics , 1998 . 17 ( 14 ): 2942 - 2944 . DOI: 10.1021/om980143i http://doi.org/10.1021/om980143i .

A. Odedra , C. J. Wu , T. B. Pratap , C. W. Huang , Y. F. Ran , R. S. Liu . Ruthenium-catalyzed aromatization of enediynes via highly regioselective nucleophilic additions on a pi-alkyne functionality. A useful method for the synthesis of functionalized benzene derivatives . J. Am. Chem. Soc. , 2005 . 127 ( 10 ): 3406 - 3412 . https://www.researchgate.net/publication/244568791_Platinum_and_Ruthenium-Catalyzed_Aromatization_of_Enediynes_via_Intramolecular-_Nucleophilic_Additions https://www.researchgate.net/publication/244568791_Platinum_and_Ruthenium-Catalyzed_Aromatization_of_Enediynes_via_Intramolecular-_Nucleophilic_Additions , .

S. Naoe , Y. Suzuki , K. Hirano , Y. Inaba , S. Oishi , N. Fujii , H. Ohno . Gold(Ⅰ)-catalyzed regioselective inter-/intramolecular addition cascade of di-and triynes for direct construction of substituted naphthalenes . J. Org. Chem. , 2012 . 77 ( 11 ): 4907 - 4916 . DOI: 10.1021/jo300771f http://doi.org/10.1021/jo300771f .

P. Nösel , V. Müller , S. Mader , S. Moghimi , M. Rudolph , I. Braun , F. Rominger , A. S. K. Hashmi . Gold-catalyzed hydroarylating cyclization of 1, 2-bis(2-iodoethynyl)benzenes . Adv. Synth. Catal. , 2015 . 357 ( 2-3 ): 500 - 506 . DOI: 10.1002/adsc.201400749 http://doi.org/10.1002/adsc.201400749 .

A. S. Hashmi , M. Wieteck , I. Braun , M. Rudolph , F. Rominger . Gold vinylidene complexes:intermolecular C(sp(3))H insertions and cyclopropanations pathways . Angew. Chem. Int. Ed. , 2012 . 51 ( 42 ): 10633 - 10637 . DOI: 10.1002/anie.201204015 http://doi.org/10.1002/anie.201204015 .

G. dos Passos Gomes , I. V. Alabugin . Drawing catalytic power from charge separation:stereoelectronic and zwitterionic assistance in the Au(Ⅰ)-catalyzed Bergman cyclization . J. Am. Chem. Soc. , 2017 . 139 ( 9 ): 3406 - 3416 . DOI: 10.1021/jacs.6b11054 http://doi.org/10.1021/jacs.6b11054 .

S. Sun , L. Dong , D. Song , B. Huang , A. Hu . Synthesis of polyphenylenes through bergman cyclization of enediynes with long chain alkyl groups . Chinese J. Polym. Sci. , 2015 . 33 ( 1 ): 184 - 191 . DOI: 10.1007/s10118-015-1566-6 http://doi.org/10.1007/s10118-015-1566-6 .

X. Cheng , J. Ma , J. Zhi , X. Yang , A. Hu . Synthesis of novel "rod-coil" brush polymers with conjugated backbones through Bergman cyclization . Macromolecules , 2010 . 43 ( 2 ): 909 - 913 . DOI: 10.1021/ma902176j http://doi.org/10.1021/ma902176j .

J. P. Johnson , D. A. Bringley , E. E. Wilson , K. D. Lewis , L. W. Beck , A. J. Matzger . Comparison of "polynaphthalenes" prepared by two mechanistically distinct routes . J. Am. Chem. Soc. , 2003 . 125 ( 48 ): 14708 - 14709 . DOI: 10.1021/ja035695t http://doi.org/10.1021/ja035695t .

B. P. Warner , S. P. Millar , R. D. Broene , S. L. Buchwald . Controlled acceleration and inhibition of Bergman cyclization by metal chlorides . Science , 1995 . 269 ( 5225 ): 814 - 816 . DOI: 10.1126/science.269.5225.814 http://doi.org/10.1126/science.269.5225.814 .

T. Kaneko , M. Takahashi , M. Hirama . Benzannelation alters the rate limiting step in enediyne cycloaromatization . Tetrahedron Lett. , 1999 . 40 ( 10 ): 2015 - 2018 . DOI: 10.1016/S0040-4039(99)00105-7 http://doi.org/10.1016/S0040-4039(99)00105-7 .

J. W. Grissom , T. L. Calkins , H. A. McMillen , Y. Jiang . Determination of the activation parameters for the Bergman cyclization of aromatic enediynes . J. Org. Chem. , 1994 . 59 ( 19 ): 5833 - 5835 . DOI: 10.1021/jo00098a055 http://doi.org/10.1021/jo00098a055 .

T. A. Zeidan , S. V. Kovalenko , M. Manoharan , I. V. Alabugin . Ortho effect in the Bergman cyclization:comparison of experimental approaches and dissection of cycloaromatization kinetics . J. Org. Chem. , 2006 . 71 ( 3 ): 962 - 975 . DOI: 10.1021/jo0520801 http://doi.org/10.1021/jo0520801 .

K. C. Nicolau , G. Zuccarello , Y. Ogawa , E. J. Schweiger , T. Kumazawa . Cyclic conjugated enediynes related to calicheamicins and esperamicins:calculations, synthesis, and properties . J. Am. Chem. Soc. , 1988 . 110 ( 14 ): 4866 - 4868 . DOI: 10.1021/ja00222a077 http://doi.org/10.1021/ja00222a077 .

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