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Progress in Chemistry 2017, Vol. 29 Issue (11): 1331-1350 DOI: 10.7536/PC170536 Previous Articles   Next Articles

• Review •

The Research in Cycloaddition Reactions of Allenic Compounds

Xiaolei Gong, Wenchao Gao, Honghong Chang, Wenlong Wei*, Xing Li*   

  1. Department of Biological and Pharmaceutical Engineering, College of Chemistry and Chemical Engineering, Taiyuan University of Technology, Taiyuan 030024, China
  • Received: Revised: Online: Published:
  • Supported by:
    The work was supported by the Natural Science Foundation of Shanxi Province (No. 201601D011028, 20130110094).
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Allene is a kind of compounds containing 1, 2-propadiene structure. In recent years, allenes and their derivatives have attracted many researchers' interest due to the unique nature. A variety of unsaturated compounds can react with allenes or their derivatives in a variety of cycloaddition reactions to prepare indole, pyridine, furan and other cyclic compounds. The recent progress in the cycloaddition reactions of allenic compounds catalyzed by different catalysts is summarized, including [4+2], [3+2], [2+2], [1+2+2], [2+2+2], [4+3], and [4+2+2] cycloaddition reactions, and the future development of allenic compounds is prospected.
Contents
1 Introduction
2[4+2] cycloaddition of allenes
2.1[4+2] cycloadditions of allenes with unsaturated ketones
2.2[4+2] cycloadditions of allenes with butadienes
2.3[4+2] cycloadditions of allenes with alkynes
2.4[4+2] cycloadditions of allenes with alkenes
2.5[4+2] cycloadditions of allenes with hydroxylamines
3[3+2] cycloaddition of allenes
3.1[3+2] cycloadditions of allenes with imines
3.2[3+2] cycloadditions of allenes with ketones
3.3[3+2] cycloadditions of allenes with alcohols
3.4[3+2] cycloadditions of allenes with butadienes
3.5[3+2] cycloadditions of allenes with aziridines
3.6[3+2] cycloadditions of allenes with alkenes
4[2+2] cycloaddition of allenes
4.1[2+2] cycloadditions of allenes with allenes
4.2[2+2] cycloadditions of allenes with alkenes
5[1+2+2] cycloaddition of allenes
6[2+2+2] cycloaddition of allenes
6.1[2+2+2] cycloadditions of allenes with alkynyl and cyanogens
6.2[2+2+2] cycloadditions of allenes with alkenyls
6.3[2+2+2] cycloadditions of allenes with isocyanates
6.4[2+2+2] cycloadditions of allenes with triazines
7[4+3] cycloaddition of allenes
8[4+2+2] cycloaddition of allenes
9 Conclusion
Key words: allenic compound, catalysis, cycloaddition, propadiene, unsaturated bond

CLC Number: 

[1] Pan F, Fu C L, Ma S M. Chin. J. Org. Chem., 2004, 24:1168.
[2] Xu S H, Wang H, Zang G X, Zheng W H, Du Y J, Wang S Y. Chin. J. Org. Chem., 2009, 29:1474.
[3] Lledó A, Pla-Quintana A, Roglans A. Chem. Soc. Rev., 2016, 45:2010.
[4] Xiong H L, Wang H, He L J, Zhang Y H, Zeng Z. Chin. J. Org. Chem., 2011, 4:466.
[5] Burton B S, Pechman H V. Chem. Ber., 1887, 20:145.
[6] Staudinger H, Ruzika L. Helv. Chim. Acta, 1924, 7:177.
[7] Clemer W D, Solomans I A. J. Am. Chem. Soc., 1952, 74:1870.
[8] Sako S, Kurahashi T, Matsubara S. Chem. Commun., 2011, 47:6150.
[9] Wang X J, Fang T, Tong X F. Angew. Chem. Int. Ed., 2011, 50:5361.
[10] Pei C K, Jiang Y, Shi M. Org. Biomol. Chem., 2012, 10:4355.
[11] Zhang D H, Shi M. ChemistryOpen, 2012, 1:215.
[12] Pei C K, Wu L, Lian Z, Shi M. Org. Biomol. Chem., 2012, 10:171.
[13] Zhang S, Luo Y C, Hu X Q, Wang Z Y, Liang Y M, Xu P F. J. Org. Chem., 2015, 80:7288.
[14] Danda A, Kesava-Reddy N, Golz C, Strohmann C, Kumar K. Org. Lett., 2016, 18:2632.
[15] Wang C, Gao Z Z, Zhou L J, Yuan C H, Sun Z H, Xiao Y M, Guo H C. Org. Lett., 2016, 18:3418.
[16] Wang L, Lv J, Zhang L, Luo S Z. Angew. Chem. Int. Ed., 2017, 56:10867.
[17] Singh L, Elango M, Subramanian V, Gupta V, Kanwal P. J. Org. Chem., 2008, 73:2224.
[18] Hussain I, Yawer M A, Appel B, Sher M, Mahal A, Villinger A, Fischer C, Langer P. Tetrahedron, 2008, 64:8003.
[19] Mauleon P, Zeldin R M, Gonzalez A Z, Toste F D. J. Am. Chem. Soc., 2009, 131:6348.
[20] González A Z, Toste F D. Org. Lett., 2010, 12:200.
[21] Gulías M, López F, Mascareñas J L. Pure Appl. Chem., 2011, 83:495.
[22] Wang Z, Xu H C, Su Q, Hu P, Shao P L, He Y, Lu Y X. Org. Lett., 2017, 19:3111.
[23] Jiang X F, Kong W Q, Chen J, Ma S M. Org. Biomol. Chem., 2008, 6:3606.
[24] Pirovano V, Decataldo L, Rossi E, Vicente R. Chem. Commun., 2013, 49:3594.
[25] Conner M L, Brown M K. Tetrahedron, 2016, 72:3759.
[26] Chen J M, Chang C J, Ke Y J, Liu R S. J. Org. Chem., 2014, 79:4306.
[27] Zhu X F, Henry C, Kwon E O. Tetrahedron, 2005, 61:6276.
[28] Fang Y Q, Jacobsen E N. J. Am. Chem. Soc., 2008, 130:5660.
[29] Zhang B, He Z R, Xu S L, Wu G P, He Z J. Tetrahedron, 2008, 64:9471.
[30] Zhao Q Y, Han X Y, Wei Y, Shi M, Lu Y X. Chem. Commun., 2012, 48:970.
[31] Clavijo E M, Carmona A T, Reissig H U, Moreno-Vargas A J, Alvarez E, Robina I. Org. Lett., 2009, 11:4778.
[32] Cai S T, Gorityala B K, Ma J M, Leow M L, Liu X W. Org. Lett., 2011, 13:1072.
[33] Tran D N, Cramer N. Angew. Chem. Int. Ed., 2013, 52:10630.
[34] Zhou W, Li X X, Li G H, Wu Y, Chen Z. Chem. Commun., 2013, 49:3552.
[35] Wilson J E, Fu G C. Angew. Chem. Int. Ed., 2006, 45:1426.
[36] Wallace D J, Sidda R L, Reamer R A. J. Org. Chem., 2007, 72:1051.
[37] Han X Y, Wang Y Q, Zhong F G, Lu Y X. J. Am. Chem. Soc., 2011, 133:1726.
[38] Chang H T, Jayanth T T, Cheng C H. J. Am. Chem. Soc., 2007, 129:4166.
[39] Li J L, Yang X J, Jiang M, Liu J T. Tetrahedron Letters, 2017, 58:3377.
[40] Tata R R, Harmata M. Org. Lett., 2016, 18:5684.
[41] López E, Lonzi G, Gonzáleza J, López L A. Chem. Commun., 2016, 52:9398.
[42] Lin T Y, Zhu C Z, Zhang P C, Wang Y D, Wu H H, Feng J J, Zhang J L. Angew. Chem. Int. Ed., 2016, 55:10844.
[43] Barluenga J, Vicente R, Barrio P, López L A, Tomás M. J. Am. Chem. Soc., 2004, 126:5974.
[44] Pinto N, Neel M, Panossian A, Retaileau P, Frison G, Voituriez A, Marinetti A. Chem. -Eur. J., 2010, 16:1033.
[45] Steurer M, Jensen K L, Worgull D, Jørgensen K A. Chem. -Eur. J., 2012, 18:76.
[46] Lee S Y, Fu Y J, Nishiguchi A, Kalek M, Fu G C. J. Am. Chem. Soc., 2015, 137:4587.
[47] Chen B, Fan W, Chai G B, Ma S M. Org. Lett., 2012, 14:3616.
[48] Mei L Y, Wei Y, Tang X Y, Shi M. J. Am. Chem. Soc., 2015, 137:8131.
[49] Zheng W F, Bora P P, Sun G J, Kang Q. Org. Lett., 2016, 18:3694.
[50] Chen K, Sun R, Xu Q, Wei Y, Shi M. Org. Biomol. Chem., 2013, 11:3949.
[51] Nada T, Yoneshige Y, Ii Y, Matsumoto T, Fujioka H, Shuto S, Arisawa M. ACS Catal., 2016, 6:3168.
[52] Inagaki F, Narita S, Hasegawa T, Kitagaki S, Mukai C. Angew. Chem. Int. Ed., 2009, 48:2007.
[53] Croatt M P, Wender P A. Eur. J. Org. Chem., 2010, 2010:19.
[54] Shafawati M T S, Inagaki F, Kawamura T, Mukai C. Tetrahedron, 2013, 69:1509.
[55] Iwata T, Inagaki F, Mukai C. Angew. Chem. Int. Ed., 2013, 52:11138.
[56] Mukai C, Takahashi Y, Ogawa K, Hayashi Y, Inagaki F. Chem. Pharm. Bull., 2014, 62:84.
[57] Haraburda E, Lledo A, Roglans A, Pla-Quintana A. Org. Lett., 2015, 17:2882.
[58] Brusoe A T, Alexanian E J. Angew. Chem. Int. Ed., 2011, 50:6596.
[59] Miura T, Morimoto M, Murakami M. J. Am. Chem. Soc., 2010, 132:15836.
[60] Ohta Y, Yasuda S, Yokogawa Y, Kurokawa K, Mukai C. Angew. Chem. Int. Ed., 2015, 54:1240.
[61] Haraburda E, Torres S, Parella T, Sol M, Pla-Quintana A. Chem. -Eur. J., 2014, 20:5034.
[62] Peng S Y, Cao S Y, Sun J T. Org. Lett., 2017, 19:524.
[63] Alonso I, Faustino H, López F, Mascareñas J L. Angew. Chem. Int. Ed., 2011, 50:11496.
[64] Lainhart B C, Alexanian E J. Org. Lett., 2015, 17:1284.
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