Palladium-Catalyzed Allylic Alkylation Reaction of α-Substituted Benzyl Nitriles with Branched Allyl Carbonates

doi:10.6023/cjoc202006007

Chinese Journal of Organic Chemistry ›› 2020, Vol. 40 ›› Issue (10): 3399-3409.DOI: 10.6023/cjoc202006007 Previous Articles Next Articles

Special Issue: 黄乃正院士七十华诞专辑

钯催化α-取代苄腈与支链烯丙基碳酸酯的烯丙基烷基化反应

张高鹏^a,d, 江阳杰^a,d, 丁昌华^b, 侯雪龙^a,c

a 中国科学院上海有机化学研究所金属有机化学国家重点实验室上海 200032;
b 上海大学化学系上海 200444;
c 中国科学院上海有机化学研究所上海-香港化学合成联合实验室上海 200032;
d 中国科学院大学北京 100049

收稿日期:2020-06-05 修回日期:2020-06-23 发布日期:2020-07-01
通讯作者: 丁昌华, 侯雪龙 E-mail:xlhou@sioc.ac.cn;dingchanghua@shu.edu.cn
基金资助:
国家自然科学基金（Nos.21532010，21772215），中国科学院先导项目（No.XDB20030100），中国科学院，上海市科委和香港裘搓基金会资助项目.

Palladium-Catalyzed Allylic Alkylation Reaction of α-Substituted Benzyl Nitriles with Branched Allyl Carbonates

Zhang Gaopeng^a,d, Jiang Yangjie^a,d, Ding Changhua^b, Hou Xuelong^a,c

a State Key Laboratory of Organometallic Chemistry, Center for Excellence in Molecular Synthesis, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032;
b Department of Chemistry, Shanghai University, Shanghai 200032;
c Shanghai-Hong Kong Joint Laboratory in Chemical Synthesis, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032;
d University of Chinese Academy of Sciences, Beijing 100049

Received:2020-06-05 Revised:2020-06-23 Published:2020-07-01
Supported by:
Project supported by the National Natural Science Foundation of China (Nos. 21532010, 21772215), the Strategic Priority Research Program of the Chinese Academy of Sciences (No. XDB20030100), the Chinese Academy of Sciences, the Technology Commission of Shanghai Municipality, and the Croucher Foundation of Hong Kong.

1. cjoc202006007辅助材料.pdf(4284KB)

Abstract

Cite this article

Zhang Gaopeng, Jiang Yangjie, Ding Changhua, Hou Xuelong. Palladium-Catalyzed Allylic Alkylation Reaction of α-Substituted Benzyl Nitriles with Branched Allyl Carbonates[J]. Chinese Journal of Organic Chemistry, 2020, 40(10): 3399-3409.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

References

[1] (a) Tsuji, J.; Takahashi, H.; Morikawa, M. Tetrahedron Lett. 1965, 6, 4387.
(b) Trost, B. M. J. Org. Chem. 2004, 69, 5813.
(c) Trost, B. M. Org. Process Res. Dev. 2012, 16, 185.
[2] (a) Pfaltz, A.; Lautens, M. In Comprehensive Asymmetric Catalysis, Vol. 2, Eds.:Jacobsen, E. N.; Pfaltz, A.; Yamamoto, H., Springer- Verlag, Berlin, 1999, p. 833.
(b) Trost, B. M. Chem. Rev. 1996, 96, 395.
(c) Trost, B. M.; Crawley, M. L. Chem. Rev. 2003, 103, 2921.
(d) Ding, C.-H.; Hou, X.-L. In Comprehensive Organic Synthesis, 2nd ed., Vol. 4, Eds.:Molander, G. A.; Knochel, P., Elsevier, Oxford, 2014, p. 648.
(e) Zhang, J.-L.; Jiang, G.-X. Acta Chim. Sinica 2018, 76, 890.
[3] (a) Hegedus, L. S.; Darlington, W. H.; Russell, C. E. J. Org. Chem. 1980, 45, 5193.
(b) Hoffmann, H. M. R.; Otte, A. R.; Wilde, A. Angew. Chem., Int. Ed. 1992, 31, 234.
(c) Hoffmann, H. M. R.; Otte, A. R.; Wilde, A.; Menzer, S.; Williams, D. J. Angew. Chem., Int. Ed. 1995, 34, 100.
[4] (a) Hayashi, T.; Konishi, M.; Yokota, K.; Kumada, M. J. Organomet. Chem. 1985, 285, 359.
(b) Tsuji, Y.; Kusui, T.; Kojima, T.; Sugiura, Y.; Yamada, N.; Tanaka, S.; Ebihara, M.; Kawamura, T. Organometallics 1998, 17, 4835.
(c) Zhang, P.; Brozek, L. A.; Morken, J. P. J. Am. Chem. Soc. 2010, 132, 10686.
(d) Le, H.; Batten, A.; Morken, J. P. Org. Lett. 2014, 16, 2096.
(e) Behenna, D. C.; Stoltz, B. M. J. Am. Chem. Soc. 2004, 126, 15044.
(f) Li, Y.-X.; Xuan, Q.-Q.; Liu, L.; Wang, D.; Chen, Y.-J.; Li, C.-J. J. Am. Chem. Soc. 2013, 135, 12536.
(g) Chen, J.-P.; Peng, Q.; Lei, B.-L.; Hou, X.-L.; Wu, Y.-D. J. Am. Chem. Soc. 2011, 133, 14180.
(h) Bai, D.-C.; Yu, F.-L.; Wang, W.-Y.; Chen, D.; Li, H.; Liu, Q.-R.; Ding, C.-H.; Chen, B.; Hou, X.-L. Nat. Commun. 2016, 7, 11806.
(i) Yu, F.-L.; Bai, D.-C.; Liu, X.-Y.; Jiang, Y.-J.; Ding, C.-H.; Hou, X.-L. ACS Catal. 2018, 8, 3317.
[5] (a) Trost, B. M.; Keinan, E. Tetrahedron Lett. 1980, 21, 2591.
(b) Trost, B. M.; Schroeder, G. M. J. Am. Chem. Soc. 1999, 121, 6759.
(c) Braun, M.; Laicher, F.; Meier, T. Angew. Chem., Int. Ed. 2000, 39, 3494.
(d) Yan, X.-X.; Liang, C.-G.; Zhang, Y.; Hong, W.; Cao, B.-X.; Dai, L.-X.; Hou, X.-L. Angew. Chem., Int. Ed. 2005, 44, 6544.
(e) Zheng, W.-H.; Zheng, B.-H.; Zhang, Y.; Hou, X.-L. J. Am. Chem. Soc. 2007, 129, 7718.
(f) Zhang, K.; Peng, Q.; Hou, X.-L.; Wu, Y.-D. Angew. Chem., Int. Ed. 2008, 47, 1741.
(g) Chen, J.-P.; Ding, C.-H.; Liu, W.; Hou, X.-L.; Dai, L.-X. J. Am. Chem. Soc. 2010, 132, 15493.
(h) Ibrahem, I.; Córdova, A. Angew. Chem., Int. Ed. 2006, 45, 1952.
(i) Trost, B. M.; Thaisrivongs, D. A. J. Am. Chem. Soc. 2008, 130, 14092.
(j) Sha, S.-C.; Zhang, J.-D.; Carroll, P. J.; Walsh, P. J. J. Am. Chem. Soc. 2013, 135, 17602.
[6] (a) Tsuji, J.; Shimizu, I.; Minami, I.; Ohashi, Y. J. Org. Chem. 1985, 50, 1523.
(b) Sawamura, M.; Sudoh, M.; Ito, Y. J. Am. Chem. Soc. 1996, 118, 3309.
(c) Evans, P. A.; Oliver, S.; Chae, J. J. Am. Chem. Soc. 2012, 134, 19314.
(d) Maji, T.; Tunge, J. K. Org. Lett. 2014, 16, 5072.
(e) Turnbull, B. W. H.; Evans, P. A. J. Am. Chem. Soc. 2015, 137, 6156.
(f) Turnbull, B. W. H.; Oliver, S.; Evans, P. A. J. Am. Chem. Soc. 2015, 137, 15374.
[7] (a) Bai, D.-C.; Liu, X.-Y.; Li, H.; Ding, C.-H.; Hou, X.-L. Chem. Asian J. 2017, 12, 212.
(b) Zhang, G.-P.; Huang S.; Jiang, Y.-J.; Liu, X.-Y.; Ding, C.-H.; Wei, Y.; Hou, X.-L. Chem. Commun. 2019, 55, 6449.
[8] Poli, G.; Prestat, G.; Liron, F.; Kammerer-Pentier, C. Top. Organomet. Chem. 2012, 38, 1.
[9] (a)Tsuji, Y.; Kusui, T.; Kojima, T.; Sugiura, Y.; Yamada, N.; Tanaka, S.; Ebihara, M.; Kawamura. T. Organometallics 1998, 17, 4835.
(b) Bai, D. C.; Wang, W. Y.; Ding, C. H.; Hou, X. L. Synlett 2015, 26, 1510.
[10] Triandafillidi, I.; Kokotou, M. G.; Kokotos, C. G. Org. Lett. 2018, 20, 36.
[11] (a) Yuan, Q.-J.; Yao, K.; Liu, D.-L.; Zhang, W.-B. Chem. Commun. 2015, 51, 11834.
(b) Hayashi, M.; Brown, L. E.; Porco, Jr. J. A. Eur. J. Org. Chem. 2016, 4800.

[1]	Hao Qin, Chuanjin Hou, Dinghua Liang, Xinwei He, Ling Li, Xiangping Hu. Chiral P,N,N-Ligands for Pd-Catalyzed Asymmetric Allylic Substitutions [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 282-290.
[2]	Xianqiang Meng, Yi Yang, Wanjie Liang, Jingtao Wang, Rongkui Zhang, Hui Liu. Palladium-Catalyzed Regioselective Aryl Phenoxylation of Allenamide [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 224-231.
[3]	Jingrui Wang, Yongkui Feng, Nengzhong Wang, Nianyu Huang, Hui Yao. Pd-Catalyzed Stereoselective Synthesis of Nitroalkyl β-C-Glycosides [J]. Chinese Journal of Organic Chemistry, 2023, 43(9): 3216-3225.
[4]	Yuchao Wang, Jinbiao Liu, Zhitao He. Palladium-Catalyzed Asymmetric Hydrofunctionalizations of Conjugated Dienes [J]. Chinese Journal of Organic Chemistry, 2023, 43(8): 2614-2627.
[5]	Meijiao Sun, Jing Tan, Yu Tan, Jinsong Peng, Chunxia Chen. Pd-Catalyzed C(2)—H Arylation of 3-(2-Aminopyrimidin-4-yl)indoles [J]. Chinese Journal of Organic Chemistry, 2023, 43(11): 3945-3959.
[6]	Wei Xiong, Bin Shi, Xuan Jiang, Liangqiu Lu, Wenjing Xiao. Ligand-Switched Pd-Catalyzed Divergent Transformations of Vinyl Cyclic Carbamates and Isocyanates [J]. Chinese Journal of Organic Chemistry, 2023, 43(1): 265-273.
[7]	Chengyao Kimmy Cao, Yaru Niu, Yunchen Jiang, Hongmei Qu, Chao Chen. Pd-Catalyzed Chlorodifluoroethylation Reaction of C—H Bond of Acetanilides with Chlorodifluoroethyl Iodonium Reagents [J]. Chinese Journal of Organic Chemistry, 2022, 42(7): 2098-2105.
[8]	Xiangyang Zhang, Qinglin Wu, Feifei Wang, Youming Shen, Yucai Tang. A Near-Infrared Fluorescent Probe with 2-Hydroxy-N,N-dimethyl- benzylamine as a New Recognition Fragment for Pd²⁺ Detection and Bioimaging [J]. Chinese Journal of Organic Chemistry, 2022, 42(6): 1786-1791.
[9]	Hong-Chao Chen, Yichen Wu, Yang Yu, Peng Wang. Pd-Catalyzed Isomerization of Alkenes [J]. Chinese Journal of Organic Chemistry, 2022, 42(3): 742-757.
[10]	Xianghui Meng, Liangru Yang, Qilin Liu, Zhenhua Dong, Jinwei Yuan, Yongmei Xiao, Pu Mao. Amide Functionalized Pyridine/Pyrimidine Chelating N-Heterocyclic Carbene Palladium Complexes: Synthesis, Structure, and Catalysis for C-5 Arylation of Imidazoles [J]. Chinese Journal of Organic Chemistry, 2022, 42(11): 3747-3756.
[11]	Xintuo Yang, Pinhong Chen, Guosheng Liu. Asymmetric Palladium-Catalyzed Aza-Wacker Reaction of Alkenes: Efficient Synthesis of Chiral 1,3-Oxazinan-2-ones [J]. Chinese Journal of Organic Chemistry, 2022, 42(10): 3382-3389.
[12]	Shihu Jia, Siyuan Chen, Zeshui Liu, Honggang Cheng, Qianghui Zhou. Pd/Novel Axially Chiral Phosphine-Alkene Ligands Catalyzed Asymmetric Allylic Alkylation of Indoles [J]. Chinese Journal of Organic Chemistry, 2022, 42(10): 3373-3381.
[13]	Jieming Zhang, Hang Ni, Qi Wu, Junfeng Yang, Junliang Zhang. Development of P, S and Si-Stereogenic Compounds Synthesis via Palladium Catalysis [J]. Chinese Journal of Organic Chemistry, 2022, 42(10): 3118-3128.
[14]	Yang Han, Weichao Jiang, Jing Zhang, Jinsong Peng, Chunxia Chen. Visible-Light-Promoted Palladium-Catalyzed C—H Amination for the Synthesis of Carbazolequinones [J]. Chinese Journal of Organic Chemistry, 2022, 42(1): 266-276.
[15]	Tao Zhang, Shangda Li, Chunlin Zhou, Xinchao Wang, Meng Zhang, Zezhong Gao, Gang Li. Site-Selective C—H Iodination of Phenol Derivatives Using Aryl Iodide as Iodinating Reagent [J]. Chinese Journal of Organic Chemistry, 2021, 41(9): 3511-3520.

钯催化α-取代苄腈与支链烯丙基碳酸酯的烯丙基烷基化反应

Palladium-Catalyzed Allylic Alkylation Reaction of α-Substituted Benzyl Nitriles with Branched Allyl Carbonates

PDF

Supporting Info.

Knowledge

Abstract

Cite this article

share this article

References

Related Articles 15

Recommended Articles

Metrics

Comments