Pd-Catalyzed Dearomative Spirocyclization of Bromophenols via[2+2+1] Strategy

doi:10.6023/cjoc201903065

Chinese Journal of Organic Chemistry ›› 2019, Vol. 39 ›› Issue (8): 2211-2217.DOI: 10.6023/cjoc201903065 Previous Articles Next Articles

Special Issue: 陈茹玉先生诞辰100周年

Articles

钯催化溴代酚的[2+2+1]去芳构螺环化反应

李锟雨, 白璐, 栾新军

西北大学化学与材料科学学院西安 710127

收稿日期:2019-03-28 修回日期:2019-04-26 发布日期:2019-05-28
通讯作者: 白璐, 栾新军 E-mail:xluan@nwu.edu.cn;bailu@nwu.edu.cn
基金资助:
国家自然科学基金（No.21672169）、西安市有机分子工程重点实验室（No.201805058ZD9CG42）资助项目.

Pd-Catalyzed Dearomative Spirocyclization of Bromophenols via[2+2+1] Strategy

Li Kunyu, Bai Lu, Luan Xinjun

College of Chemistry & Materials Science, Northwest University, Xi'an 710127

Received:2019-03-28 Revised:2019-04-26 Published:2019-05-28
Contact: 10.6023/cjoc201903065 E-mail:xluan@nwu.edu.cn;bailu@nwu.edu.cn
Supported by:
Project supported by the National Natural Science Foundation of China (No. 21672169), and the Key Laboratory Project of Xi'an City (No. 201805058ZD9CG42).

1. Pd-Catalyzed Dearomative Spirocyclization of Bromophenols via[2+2+1] Strategy.PDF(5291KB)

Abstract

A novel palladium(0)-catalyzed dearomative spirocyclization reaction of bromophenols has been developed for building a series of spirocyclic architectures containing a quaternary carbon center via[2+2+1] strategy. This method employs inexpensive bromophenols and easily accessible alkynes. It exhibits a broad substrate scope in good yields. Notably, this transformation can be realized with high regioselectivity (>19:1 rr) when using unsymmetrical alkynes, which greatly expands the research scope of phenol dearomatization.

Key words: transition-metal-catalyzed, dearomatization, spirocyclization, bromophenols

Cite this article

Li Kunyu, Bai Lu, Luan Xinjun. Pd-Catalyzed Dearomative Spirocyclization of Bromophenols via[2+2+1] Strategy[J]. Chinese Journal of Organic Chemistry, 2019, 39(8): 2211-2217.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

References

[1] (a) Edrada, R. A.; Stessman, C. C.; Crews, P. J. Nat. Prod. 2003, 66, 939.
(b) Cheng, P.; Ma, Y.; Yao, S.; Zhang, Q.; Wang, E.; Yan, M.; Zhang, X.; Zhang, F.; Chen, J. Bioorg. Med. Chem. Lett. 2007, 17, 5316.
(c) Zhang, Y.; Ge, H.; Zhao, W.; Dong, H.; Xu, Q.; Li, S.; Li, J.; Zhang, J.; Song, Y.; Tan, R. Angew. Chem., Int. Ed. 2008, 47, 5823.
(d) Fu, J.; Qin, J.; Zeng, Q.; Huang, Y.; Jin, H.; Zhang, W. Chem. Pharm. Bull. 2010, 58, 1263.
(e) Zhao, J. H.; Wang, Z. Q.; Zhou, Y.; Zhu, G. N.; Yu, C. M. Chin. J. Org. Chem. 2011, 31, 3031(in Chinese). (赵金浩,王宗成,周勇,朱国念,俞传明,有机化学, 2011, 31, 3031.)
(f) Park, H. B.; Kim, Y.-J.; Lee, J. K.; Lee, K. R.; Kwon, H. C. Org. Lett. 2012, 14, 5002.
(g) Du, W.; Hung, H.; Kuo, P.; Hwang, T.; Shiu, L.; Shiu, K.; Lee, E.; Tai, S.; Wu, T. Org. Lett. 2016, 18, 3042.
(h) Ma, Y.; Fan, C.; Chin. J. Org. Chem. 2016, 36, 2380(in Chinese). (马养民,范超,有机化学, 2016, 36, 2380.)
[2] Reviews:(a) Roche, S. P.; Porco, Jr., J. Angew. Chem., Int. Ed. 2011, 50, 4068.
(b) Zhuo, C.; Zhang, W.; You, S. Angew. Chem., Int. Ed. 2012, 51, 12662.
(c) Wu, W.-T.; Zhang, L.; You, S.-L. Chem. Soc. Rev. 2016, 45, 1570.
(d) James, M. J.; O'Brien, P.; Taylor, R. J. K.; Unsworth, W. P. Chem. Eur. J. 2016, 22, 2856.
(e) Nemoto, T.; Hamada, Y. Synlett 2016, 2301.
(f) Wang, H.; Luan, X. Org. Biomol. Chem. 2016, 14, 9451.
(g) Liang, X.-W.; Chen, X.; Zhang, Z.; You S.-L. Chin. Chem. Lett. 2018, 29, 1212.
(h) Wang, K.-K.; Du, W.; Zhu, J.; Chen Y.-C. Chin. Chem. Lett. 2017, 28, 512.
(i) Wu, W.-T.; Zhang, L. M.; You, S.-L. Acta Chim. Sinica 2017, 75, 419(in Chinese). (吴文挺,张立明,游书力,化学学报, 2017, 75, 419.)
[3] (a) Tyman, J. H. P. Synthetic and Natural Phenol; Elsevier:New York, 1996.
(b) Rappoport, Z. The Chemistry of Phenols; John Wiley & Sons Ltd.:Chichester, 2003.
(c) Weber, M.; Weber, M.; KleineBoymann, M. Phenol. In Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH, Weinheim, 2004.
[4] For selected reviews, see:(a) Kündig, E. P.; Rape, A. Top. Organomet. Chem. 2004, 7, 95.
(b) Quideau, S.; Pouységu, L.; Deffieus, D. Synlett 2008, 467.
(c) Roche, S. P.; Porco, J. A., Jr. Angew. Chem., Int. Ed. 2011, 50, 4068.
(d) Zhuo, C. X.; Zhang, W.; You, S. L. Angew. Chem., Int. Ed. 2012, 51, 12662.
(e) Lü, W. W.; He, X. C.; Shi, M.; Wang, F. J. Chin. J. Org. Chem. 2019, 39, 532(in Chinese). (吕雯雯,贺信淳,施敏,王飞军,有机化学, 2019, 39, 532.)
(f) Cui, N.; Zhao, Y.; Wang, Y. X. Chin. J. Org. Chem. 2017, 37, 20(in Chinese). (崔娜,赵宇,王云侠,有机化学, 2017, 37, 20.)
(g) Lin, S. B.; He, X. R.; Meng, J. P.; Gu, H. N.; Zhang, P. Z.; Wu, J. Chin. J. Org. Chem. 2017, 37, 1864(in Chinese). (蔺松波,何兴瑞,孟金鹏,顾海宁,张培志,吴军,有机化学, 2017, 37, 1864.)
[5] (a) Roche, S. P.; Porco, J., Jr Angew. Chem., Int. Ed. 2011, 50, 4068.
(b) Zhuo, C.; Zhang, W.; You, S. Angew. Chem., Int. Ed. 2012, 51, 12662.
(c) Zhuo, C.; Zheng, C.; You, S. Acc. Chem. Res. 2014, 47, 2558.
(d) Zheng, C.; You, S. Chem. 2016, 1, 830.
(e) Wu, W.; Zhang, L.; You, S. Chem. Soc. Rev. 2016, 45, 1570.
(f) Nemoto, T.; Hamada, Y. Synlett 2016, 27, 2301.
(g) Wang, H.; Luan, X. Org. Biomol. Chem. 2016, 14, 9451.
[6] Nemoto, T.; Ishige, Y.; Yoshida, M.; Kohno, Y.; Kanematsu, M.; Hamada, Y. Org. Lett. 2010, 12, 5020.
[7] Rousseaux, S.; García-Fortanet, J.; Del Aguila Sanchez, M. A.; Buchwald, S. L. J. Am. Chem. Soc. 2011, 133, 9282.
[8] Wu, Q.; Liu, W.; Zhuo, C.; Rong, Z.; Ye, K.; You, S. Angew. Chem., Int. Ed. 2011, 50, 4455.
[9] (a) Nan, J.; Zuo, Z.; Luo, L.; Bai, L.; Zheng, H.; Yuan, Y.; Liu, J.; Luan, X.; Wang, Y. J. Am. Chem. Soc. 2013, 135, 17306.
(b) Zuo, Z.; Yang, X.; Liu, J.; Nan, J.; Bai, L.; Wang, Y.; Luan, X. J. Org. Chem. 2015, 80, 3349.
[10] Seoane, A.; Casanova, N.; Quiñones, N.; Mascareñas, J. L.; Gulías, M. J. Am. Chem. Soc. 2014, 136, 7607.
[11] Kujawa, S.; Best, D.; Burns, D. J.; Lam, H. W. Chem. Eur. J. 2014, 20, 8599.
[12] (a) Zheng, J.; Wang, S.; Zheng, C.; You, S. J. Am. Chem. Soc. 2015, 137, 4880.
(b) Zheng, C.; Zheng, J.; You, S. ACS Catal. 2016, 6, 262.
[13] Gu, S.; Luo, L.; Liu, J.; Bai, L.; Zheng, H.; Wang, Y.; Luan, X. Org. Lett. 2014, 16, 6132.
[14] Bai, L.; Yuan, Y.; Liu, J.; Wu, J.; Han, L.; Wang, H.; Wang, Y.; Luan, X. Angew. Chem., Int. Ed. 2016, 55, 6946.

[1]	Jing Tang, Wenkun Luo, Jun Zhou. Advances in the Synthesis of Azaspiro[4.5]trienones [J]. Chinese Journal of Organic Chemistry, 2023, 43(9): 3006-3034.
[2]	Jun Lu, Qichuang Li, Renxiao Liang, Yixia Jia. Nickel-Catalyzed Intramolecular Dearomative Arylation of Pyridiniums and Quinoliniums [J]. Chinese Journal of Organic Chemistry, 2023, 43(5): 1875-1882.
[3]	Mingyang Pang, Honghong Chang, Zhang Feng, Juan Zhang. Recent Advances in Transition-Metal-Catalyzed Tandem Dearomatization of Indoles [J]. Chinese Journal of Organic Chemistry, 2023, 43(4): 1271-1291.
[4]	Chengfu Zeng, Yuan He, Qing Li, Lin Dong. Ir(III)-Catalyzed Novel Three-Component Cascade Trifluoroethoxylation and One-Pot Method to Construct Complex Amide Compounds [J]. Chinese Journal of Organic Chemistry, 2023, 43(3): 1115-1123.
[5]	Peng Liu, Fuming Zhong, Lihao Liao, Weiqiang Tan, Xiaodan Zhao. Progress in the Construction of Spirocyclohexadienones via Alkyne-Involving Dearomatization [J]. Chinese Journal of Organic Chemistry, 2023, 43(12): 4019-4035.
[6]	Junxiu Liang, Yazhou Liu, Amu Wang, Yanchao Wu, Xiaofeng Ma, Huijing Li. Dearomatization of Halonaphthols via an Intermolecular [4＋1] Spiroannulation with in situ Formed Aza-ortho-quinone Methides [J]. Chinese Journal of Organic Chemistry, 2023, 43(11): 3888-3899.
[7]	Huaiyuan Zhang, Nuo Xu, Rongping Tang, Xingli Shi. Recent Advances in Asymmetric Dearomatization Reactions Induced by Chiral Hypervalent Iodine Reagents [J]. Chinese Journal of Organic Chemistry, 2023, 43(11): 3784-3805.
[8]	Haoyang Liu, Shuangshuang Sun, Xianli Ma, Yanyan Chen, Yanli Xu. Synthesis of Selenylated Spiro[indole-3,3'-quinoline] Derivatives via Visible-Light-Promoted Isocyanide Insertion [J]. Chinese Journal of Organic Chemistry, 2022, 42(9): 2867-2876.
[9]	Rong Wang, Lichen Xu, Yi Lu, Bo Jiang, Wenjuan Hao. Sc(OTf)₃-Catalyzed Dearomatization of Indoles for the Synthesis of 3,3'-Bisindoles [J]. Chinese Journal of Organic Chemistry, 2021, 41(4): 1582-1590.
[10]	Qiang Yan, Rong Fan, Binbin Liu, Shuaisong Su, Bo Wang, Tuanli Yao, Jiajing Tan. Recent Progress in Aryne Participated Dearomatization Reactions [J]. Chinese Journal of Organic Chemistry, 2021, 41(2): 455-470.
[11]	Yuchao Wang, Jinbiao Liu, Guanyinsheng Qiu, Yu Yang, Hongwei Zhou. Metal-Free Selenizative spiro-Tricyclization of N-Hydroxylethyl-N-arylpropiolamides [J]. Chinese Journal of Organic Chemistry, 2021, 41(12): 4798-4807.
[12]	Jun Lu, Renxiao Liang, Yixia Jia. Copper-Catalyzed Intramolecular Dearomative Arylation of Naphthylamines [J]. Chinese Journal of Organic Chemistry, 2021, 41(10): 4007-4013.
[13]	Yinjun Huang, Jinshan Li, Shen Li, Junan Ma. Cobalt-Catalyzed Aerobic Oxidative Dearomatization of 2-Aryl Indoles and in situ [3+2] Annulation with Enamides [J]. Chinese Journal of Organic Chemistry, 2021, 41(10): 4028-4038.
[14]	Xu-Xu Qing-Feng, Huang Xian-Yun, Zhang Xiao, You Shu-Li. Synthesis of 1,2-Dihydroquinolines by Reduction of Quinolines with Sodium Cyanoborohydride [J]. Chinese Journal of Organic Chemistry, 2020, 40(10): 3446-3451.
[15]	Wang Yonggang, Liu Renrong, Gao Jianrong, Jia Yixia. Palladium-Catalyzed Dearomative Decarboxylative Alkynylation of Indoles with Acetylenecarboxylic Acids [J]. Chin. J. Org. Chem., 2017, 37(3): 691-697.

钯催化溴代酚的[2+2+1]去芳构螺环化反应

Pd-Catalyzed Dearomative Spirocyclization of Bromophenols via[2+2+1] Strategy

PDF

Supporting Info.

Knowledge

Abstract

Cite this article

share this article

References

Related Articles 15

Recommended Articles

Metrics

Comments