Phosphine Oxide-Directed Palladium-Catalyzed Heck-Type Functionalization of o-Carboranes

doi:10.6023/cjoc202103015

Chinese Journal of Organic Chemistry ›› 2021, Vol. 41 ›› Issue (8): 3249-3255.DOI: 10.6023/cjoc202103015 Previous Articles Next Articles

ARTICLES

膦氧导向钯催化邻碳硼烷Heck类型的官能团化反应

连凌翔, 尹静怡, 林彩霞^*(), 叶克印, 袁耀锋^*()

福州大学化学学院福州 350108

收稿日期:2021-03-06 修回日期:2021-04-16 发布日期:2021-05-08
通讯作者: 林彩霞, 袁耀锋
基金资助:
国家自然科学基金(21772023); 国家自然科学基金(21901041)

Phosphine Oxide-Directed Palladium-Catalyzed Heck-Type Functionalization of o-Carboranes

Lingxiang Lian, Jingyi Yin, Caixia Lin(), Keyin Ye, Yaofeng Yuan()

College of Chemistry, Fuzhou University, Fuzhou 350108

Received:2021-03-06 Revised:2021-04-16 Published:2021-05-08
Contact: Caixia Lin, Yaofeng Yuan
Supported by:
National Natural Science Foundation of China(21772023); National Natural Science Foundation of China(21901041)

1. .pdf(1750KB)

Abstract

The selective functionalization of o-carboranes is a popular topic in carborane chemistry. o-Carborane has been widely used in aggregation-induced luminescent materials, nonlinear luminescent materials and other function materials due to its special 3D-aromaticity. The π conjugated systems-tethered o-carboranes could further broaden its applications in the field of luminescent materials. Herein, we have developed a palladium-catalyzed Heck-type mono-alkenylation of o-carboranes featuring phosphine oxide as the directing group.

Key words: palladium, Heck reaction, carborane, B—H activation

Cite this article

Lingxiang Lian, Jingyi Yin, Caixia Lin, Keyin Ye, Yaofeng Yuan. Phosphine Oxide-Directed Palladium-Catalyzed Heck-Type Functionalization of o-Carboranes[J]. Chinese Journal of Organic Chemistry, 2021, 41(8): 3249-3255.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

Fig. & Tab. 6

Scheme 1. Transition-metal-catalyzed B—H bond functionalization of o-carboranes

Entry	Cat.	Ag salt	x	Yield^b/%
1	Pd(OAc)₂	AgOAc	2	<5
2	Pd(TFA)₂	AgOAc	2	13
3	Pd(OAc)₂	AgTFA	2	21
4	Pd(TFA)₂	AgTFA	2	32
5 ^c	Pd(TFA)₂	AgTFA	3	46
6^c^,^d	Pd(TFA)₂	AgTFA	3	54 (46) ^e

Table 1. Reaction condition optimizationa

Figure 1. X-ray diffraction analysis of 3

Table 2. Substrate scope of the palladium-catalyzed B(4)-alkenylation of o-carboranesa

Scheme 2. Unsuccessful substrates

Scheme 3. Proposed mechanism

References 14

[15]	Popescu, A.-R.; Laromaine, A.; Teixidor, F.; Sillanpää, R.; Kivekäs, R.; Llambias, J. I.; Viñas, C. Chem.-Eur. J. 2011, 17, 4429. doi: 10.1002/chem.v17.16
[1]	(a) Liu, L. J.; Mak T, C. W.; Zang, S. Q. Chin. J. Chem. 2021, 39, 81. doi: 10.1002/cjoc.v39.1
	(b) Kolel-Veetil, M. K.; Beckham, H. W.; Keller, T. M. Chem. Mater. 2004, 16, 3162. doi: 10.1021/cm035348i
	(c) Gao, Y.; Cui, P. F.; Aznarez, F.; Jin, G. X., Chem.-Eur. J. 2018, 24, 10357. doi: 10.1002/chem.201801381
	(d) Armstrong, A. F.; Valliant, J. F. Dalton Trans. 2007, 38, 4240.
[2]	(a) Cui, P.-F.; Lin, Y. J.; Li, Z. H.; Jin, G.-X. J. Am. Chem. Soc. 2020, 142, 8532. doi: 10.1021/jacs.0c03176
	(b) Guo, S.-T.; Cui, P.-F.; Yuan, R.-Z.; Jin, G.-X. Chem. Commun. 2021, 57, 2412. doi: 10.1039/D0CC08290B
[3]	(a) Xiong, H. J.; Li, Y. R.; Ye, H. H.; Huang, G.; Zhou, D. F.; Huang, Y. B. J. Mater. Chem. B 2020, 8, 10309. doi: 10.1039/D0TB01886D
	(b) Zhang, J.; Liu, K.; Liu, Z. S.; Wang, Z. L.; Hua, C. X.; Liu, T. H.; Fang, Y. ACS Appl. Mater. Inter. 2021, 13, 5625. doi: 10.1021/acsami.0c21424
	(c) Yao, Z. J.; Jin, Y.-X.; Deng, W.; Liu, Z.-J. Inorg. Chem. 2021, 60, 2756. doi: 10.1021/acs.inorgchem.0c03625
[4]	Sarosi, M.-B.; Neumann, W.; Lybrand, T. P.; Hey-Hawkins, E. J. Chem. Inf. Model. 2017, 57, 2056.
[5]	(a) Zhang, J; Xie, Z. W. Chin. J. Chem. 2018, 36, 1041. doi: 10.1002/cjoc.201800355
	(b) Chan, T L; Xie, Z. Chem. Sci. 2018, 9, 2284. doi: 10.1039/C7SC04722C
	(c) Guo, J. X.; Liu, D. Q.; Zhang, J. H.; Zhang, J. J.; Miao, Q.; Xie, Z. W. Chem. Commun. 2015, 51, 12004. doi: 10.1039/C5CC03608A
	(d) Tu, D. S.; Cai, S. Z.; Fernandez, C.; Ma, H. L.; Wang, X.; Wang, H.; Ma, C. Q.; Yan, H.; Lu, C. S.; An, Z. F. Angew Chem. Int. Ed. 2019, 58, 9129. doi: 10.1002/anie.v58.27
	(e) Wei, X.; Zhu, M. J.; Cheng, Z.; Lee, M.; Yan, H.; Lu, C. S.; Xu, J. J. Angew. Chem. Int. Ed. 2019, 58, 3162. doi: 10.1002/anie.v58.10
[6]	(a) Wang, Z. J.; Zhao, J. W.; Muddassir, M.; Guan, R. F.; Tao, S. L. Inorg. Chem. 2021, 60, 4705. doi: 10.1021/acs.inorgchem.0c03664
	(b) Li, X.; Zhou, Q.; Zhu, M.; Chen, W.; Wang, B. B.; Sha, Y.; Yan, H. Chem.-Asian J. 2021, 7, 757.
	(c) Ochi, J.; Tanaka, K.; Chujo, Y. Angew. Chem. Int. Ed. 2020, 25, 9841.
	(d) Nishino, K.; Tanaka, K.; Chujo, Y. Asian J. Org. Chem. 2019, 12, 2228.
[7]	(a) Chen, Y.; Au, Y. K.; Quan, Y. J.; Xie, Z. W. Sci. China Chem. 2019, 62, 74. doi: 10.1007/s11426-018-9388-3
	(b) Zheng, F. R.; Leung, T. F.; Chan, K. W.; Sung, H. H. Y.; Williams, I. D.; Xie, Z. W.; Jia, G. C. Chem. Commun. 2016, 52, 10767. doi: 10.1039/C6CC05283E
	(c) Lyu, H. R.; Quan, Y. J.; Xie, Z. W. Angew. Chem. Int. Ed. 2015, 54, 10623. doi: 10.1002/anie.201504481
	(d) Zhao, D.; Zhang, J. J.; Xie, Z. W. Chem.-Eur. J. 2015, 21, 10334. doi: 10.1002/chem.201501911
[8]	(a) Kürti, L.; Czakó, B. Strategic Applications of Named Reactions in Organic Synthesis:Background and Detailed Mecnisms, Elsevier Academic Press, Burlington, 2007,p. 196.
	(b) Huang, X. L.; Teng, S. H.; Chi, Y. R.; Xu, W. Q.; Pu, M. P.; Wu, Y. D.; Zhou, J. S. Angew. Chem. Int. Ed. 2020, 60, 2828. doi: 10.1002/anie.v60.6
	(c) Peng, X. P.; Yang, Y.; Luo, B. L.; Wen, S. J.; Huang, P. Adv. Syn. Catal. 2021, 363, 222. doi: 10.1002/adsc.v363.1
	(d) Ju, B. H.; Chen, S. G.; Kong, W. Q. Org. Lett. 2019, 21, 9343. doi: 10.1021/acs.orglett.9b03517
	(e) Zhou, L. X.; Shi, Y. X.; Zhu, X. Y.; Zhang, P. Tetrahedron Lett. 2019, 60, 2005.
	(f) Xie, J.-Q.; Liang, R.-X.; Jia, Y.-X. Chin. J. Chem. 2021, 3, 710.
	(g) Yang, P.; Xu, R.-Q.; Zheng, C.; You, S.-L. Chin. J. Chem. 2020, 3, 235.
	(h) Liu, C. X.; Liu, G. Y.; Zhao, H. K. Chin. J. Chem. 2016, 10, 1048.
[9]	(a) Wen, Z. K.; Zhao, Z. K.; Wang, N. J.; Chen, Z. L.; Chao, J. B.; Feng, L. H. Org. Lett. 2019, 21, 9545. doi: 10.1021/acs.orglett.9b03721
	(b) Bettadapur, K. R.; Sherikar, M. S.; Lanke, V.; Prabhu, K. R. Asian J. Org. Chem. 2018, 7, 1338. doi: 10.1002/ajoc.v7.7
[10]	Grimes, R. N. Carboranes, 3rd ed., Elsevier, Oxford, 2016.
[11]	(a) Wu, J.; Cao, K.; Xu, T.-T.; Zhang, X.-J.; Jiang, L.; Yang, J. X.; Huang, Y. W. RSC Adv. 2015, 5, 91683. doi: 10.1039/C5RA18555F
	(b) Lyu, H. R.; Quan, Y. J.; Xie, Z. W. Angew. Chem. Int. Ed. 2015, 54, 10623. doi: 10.1002/anie.201504481
	(c) Zhang, C. Y.; Wang, Q.; Tian, S.; Zhang, J. W.; Li, J. Y.; Zhou, L.; L, J. Org. Biomol. Chem. 2020, 18, 4723. doi: 10.1039/D0OB00698J
	(d) Wang, Q.; Tian, S.; Zhang, C. Y.; Li, J. W.; Wang, Z. X.; Du, Y. M.; Zhou, L.; L, J. Org. Lett. 2019, 21, 8018. doi: 10.1021/acs.orglett.9b03009
[12]	(a) Quan, Y. J.; Xie, Z. W. J. Am. Chem. Soc. 2014, 136, 15513. doi: 10.1021/ja509557j
	(b) Quan, Y. J.; Xie, Z. W. Angew. Chem. Int. Ed. 2016, 55, 1295. doi: 10.1002/anie.201507697
	(c) Lyu, H. R.; Quan, Y. J.; Xie, Z. W. Angew. Chem. Int. Ed. 2016, 128, 12019. doi: 10.1002/ange.201605880
	(d) Lyu, H. R.; Quan, Y. J.; Xie, Z. W. J. Am. Chem. Soc. 2016, 138, 12727. doi: 10.1021/jacs.6b07086
	(e) Lyu, H. R.; Quan, Y. J.; Xie, Z. W. Chem.-Eur. J. 2017, 23, 14866. doi: 10.1002/chem.201703006
	(f) Baek, Y.; Kim, S. H.; Son, J.-Y.; Lee, K. Y.; Kim, D. W.; Lee, P. H. ACS Catal. 2019, 9, 10418. doi: 10.1021/acscatal.9b03380
[13]	(a) Xu, T.-T.; Cao, K.; Zhang, C.-Y.; Wu, J.; Ding, L.-F.; Yang, J. X. Org. Lett. 2019, 21, 9276. doi: 10.1021/acs.orglett.9b03790
	(b) Xu, T.-T.; Cao, K.; Zhang, C.-Y.; Wu, J.; Jiang, L. H.; Yang, J. X. Chem. Commun. 2018, 54, 13603. doi: 10.1039/C8CC08193J
	(c) Liang, Y.-F.; Yang, L.; Jei, B. B.; Kuniyila, R.; Ackermann, L. Chem. Sci. 2020, 11, 10764. doi: 10.1039/D0SC01515F
	(d) Lyu, H. R.; Zhang, J.; Yang, J. T.; Quan, Y. J.; Xie, Z. W. J. Am. Chem. Soc. 2019, 141, 4219. doi: 10.1021/jacs.9b00302
[14]	Lian, L. X.; Lin, C. X.; Yu, Y.; Ye, K.-Y.; Yuan Y. F. Tetrahedron Lett. 2020, 61, 152625. doi: 10.1016/j.tetlet.2020.152625

膦氧导向钯催化邻碳硼烷Heck类型的官能团化反应

Phosphine Oxide-Directed Palladium-Catalyzed Heck-Type Functionalization of o-Carboranes

RichHTML

PDF

Supporting Info.

Knowledge

Abstract

Cite this article

share this article

Fig. & Tab. 6

References 14

Related Articles 15

Recommended Articles

Metrics

Comments

[1]	Yatong Fu, Chaofan Sun, Dan Zhang, Chengguo Jin, Juyou Lu. Recent Progress in B—H Bond Functionalization of nido-Carboranes [J]. Chinese Journal of Organic Chemistry, 2024, 44(2): 438-447.
[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]	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.
[4]	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.
[5]	Wei Xu, Hongbin Zhai, Bin Cheng, Taimin Wang. Visible Light-Induced Pd-Catalyzed Heck Reactions [J]. Chinese Journal of Organic Chemistry, 2023, 43(9): 3035-3054.
[6]	Yuchao Wang, Jinbiao Liu, Zhitao He. Palladium-Catalyzed Asymmetric Hydrofunctionalizations of Conjugated Dienes [J]. Chinese Journal of Organic Chemistry, 2023, 43(8): 2614-2627.
[7]	Hairui Jia, Zaozao Qiu. Recent Advances in Transition Metal-Catalyzed B—H Bond Activation for Synthesis of o-Carborane Derivatives with B—Heteroatom Bond [J]. Chinese Journal of Organic Chemistry, 2023, 43(3): 1045-1068.
[8]	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.
[9]	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.
[10]	Xuqun Zeng, Qian Zhang, Xufeng Wu, Jingfeng Zhang, Xinwei Zhang, Xiaolei Huang. Nickel-Catalyzed Heck Reaction of Cycloalkenes with Inert C—O Bonds of Aryl Carbonates and Aryl Sulfamates [J]. Chinese Journal of Organic Chemistry, 2022, 42(9): 2981-2987.
[11]	Binghan Lin, Jibin Zhuo, Caixia Lin, Yong Gao, Yaofeng Yuan. Synthesis and Nucleotide Recognition Properties of Carborane-Based Benzoimidazolium Cyclophane [J]. Chinese Journal of Organic Chemistry, 2022, 42(8): 2551-2558.
[12]	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.
[13]	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.
[14]	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.
[15]	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.