Promotion Mechanism of H2O for Stereoselectivity in Pd(II)-catalyzed C—H Arylation of Diarylphosphinamides with Arylboronic Acids

doi:10.1007/s40242-019-9013-9

Chemical Research in Chinese Universities ›› 2020, Vol. 36 ›› Issue (5): 843-846.doi: 10.1007/s40242-019-9013-9

• Articles • Previous Articles Next Articles

Promotion Mechanism of H₂O for Stereoselectivity in Pd(II)-catalyzed C-H Arylation of Diarylphosphinamides with Arylboronic Acids

CAI Yanchun, JIAO Long, QIU Xuepeng, DU Zhijun

Polymer Composites Engineering Laboratory, Changchun Institute of Applied Chemistry, Chinese Academy of Sciences, Changchun 130022, P. R. China

Received:2019-10-20 Revised:2019-11-16 Online:2020-10-01 Published:2020-10-01
Contact: DU Zhijun E-mail:dzj1126@ciac.ac.cn
Supported by:
Supported by the National Natural Science Foundation of China(No.21772190).

Abstract

Abstract: On the basis of a series of control experiments and nuclear magnetic resonance analyses, it is discovered that Boc-protected amino acid ligand coordinated to Pd center is partly replaced by N,N-dimethylformamide, and H₂O can inhibit coordination of N,N-dimethylformamide to Pd center. The novel action mechanism perfectly explains H₂O promotion for stereoselectivity in Pd(II)-catalyzed C-H arylation of diarylphosphinamides with arylboronic acids.

Key words: C-H activation, Stereoselectivity, Water, Ligand exchange

CAI Yanchun, JIAO Long, QIU Xuepeng, DU Zhijun. Promotion Mechanism of H₂O for Stereoselectivity in Pd(II)-catalyzed C-H Arylation of Diarylphosphinamides with Arylboronic Acids[J]. Chemical Research in Chinese Universities, 2020, 36(5): 843-846.

References 14

[1]	Quan Y. J., Xie Z. W., Chem. Soc. Rev., 2019, 48(13), 3660
[2]	Harry N. A., Saranya S., Ujwaldev S. M., Anilkumar G., Catal. Sci. Technol., 2019, 9(8), 1726
[3]	Wang W., Lorion M. M., Shah J., Kapdi A. R., Ackermann L., Angew. Chem. Int. Ed., 2018, 57(45), 14700
[4]	He J., Wasa M., Chan K. S. L., Shao O., Yu J. Q., Chem. Rev., 2017, 117(13), 8754
[5]	Zhu R. Y., Farmer M. E., Chen Y. Q., Yu J. Q., Angew. Chem. Int. Ed., 2016, 55(36), 10578
[6]	Chen X., Engle K. M., Wang D. H., Yu J. Q., Angew. Chem. Int. Ed., 2009, 48(28), 5094
[7]	Saint-Denis T. G., Zhu R. Y., Chen G., Wu Q. F., Yu J. Q., Science, 2018, 359(6377), 759
[8]	Giri R., Shi B. F., Engle K. M., Maugel N., Yu J. Q., Chem. Soc. Rev., 2009, 38(11), 3242
[9]	Gao D. W., Gu Q., Zheng C., You S. L., Acc. Chem. Res., 2017, 50(2), 351
[10]	Musaev D. G., Kaledin A., Shi B. F., Yu J. Q., J. Am. Chem. Soc., 2012, 134(3), 1690
[11]	Chen Y. H., Qin X. L., Guan J., Du Z. J., Han F. S., Tetrahedron:Asymmetry, 2017, 28(4), 522
[12]	Guan J., Wu G. J., Han F. S., Chem. Eur. J., 2014, 20(12), 3301
[13]	Du Z. J., Guan J., Wu G. J., Xu P., Gao L. X., Han F. S., J. Am. Chem. Soc., 2015, 137(2), 632
[14]	Chu L., Wang X. C., Moore C. E., Rheingold A. L., Yu J. Q., J. Am. Chem. Soc., 2013, 135(44), 16344

[1]	ZHANG Xinyu, TANG Pengpeng, ZHAI Guangyao, LIN Xiu, ZHANG Qiang, CHEN Jiesheng, WEI Xiao. Regulating Phase Junction and Oxygen Vacancies of TiO₂ Nanoarrays for Boosted Photoelectrochemical Water Oxidation [J]. Chemical Research in Chinese Universities, 2022, 38(5): 1292-1300.
[2]	ZHANG Ziqi, WANG Hanbo, LI Yuxin, XIE Minggang, LI Chunguang, LU Haiyan, PENG Yu, and SHI Zhan. Confined Pyrolysis Synthesis of Well-dispersed Cobalt Copper Bimetallic Three-dimensional N-Doped Carbon Framework as Efficient Water Splitting Electrocatalyst [J]. Chemical Research in Chinese Universities, 2022, 38(3): 750-757.
[3]	WEI Dawei, ZHANG Guangjie, LU Xiaoquan, and QIU Xiaohui. Friction of MoO₃ Nanoflakes on Graphite Surface with an Ace-like Intercalation Layer [J]. Chemical Research in Chinese Universities, 2022, 38(3): 769-773.
[4]	SONG Lili, LI Hui, LI Ting, XU Jiaquan and CHEN Huanwen. Sequential Speciation Analysis of Heavy Metals in Drinking Water Pipe Scales by Mass Spectrometry [J]. Chemical Research in Chinese Universities, 2022, 38(3): 774-781.
[5]	SHI Chao, WANG Jiaze, LI Lin, LI Yi. High-throughput Screening of Aluminophosphate Zeolites for Adsorption Heat Pump Applications [J]. Chemical Research in Chinese Universities, 2022, 38(1): 161-166.
[6]	LUAN Xiaoyu, XUE Yurui. Nickel(hydro) oxide/graphdiyne Catalysts for Efficient Oxygen Production Reaction [J]. Chemical Research in Chinese Universities, 2021, 37(6): 1268-1274.
[7]	CHEN Hongyan, WANG Junjun, WANG Ruili, ZHU Meifang. Synthesis of Fluorinated Urchin-like Serried Hydroxyapatite with Improved Water Sorption-Solubility and Bioactivity for Dental Composites [J]. Chemical Research in Chinese Universities, 2021, 37(5): 1092-1100.
[8]	YU Ruomeng, SHI Yongzheng, YANG Dongzhi. Oil-Water Separation Performance of Electrospray Reduced Graphene Oxide Microspheres with a Local Radially Aligned and Porous Structure [J]. Chemical Research in Chinese Universities, 2021, 37(3): 528-534.
[9]	XIN Rui, MA Hongyang, Shyam VENKATESWARAN, Benjamin S. HSIAO. Electrospun Nanofibrous Adsorption Membranes for Wastewater Treatment: Mechanical Strength Enhancement [J]. Chemical Research in Chinese Universities, 2021, 37(3): 355-365.
[10]	JIA Yueran, GONG Shun, ZHANG Shu, ZHAO Shikun, QIN Zhen, PAN Kai. Design, Preparation and Properties of Bio-inspired Hierarchical Structure Yarns with Enhanced Thermal Insulation and Water Transfer Ability [J]. Chemical Research in Chinese Universities, 2021, 37(3): 558-564.
[11]	XIANG Huilin, ZHONG Lingling, REN Yongqing, LIU Dongmei, ZHU Zhigao, XU Ying, WANG Yu, WANG Wei. Superhydrophobized Polyacrylonitrile/Hierarchicall-FeOOH Nanofibrous Membrane for High-salinity Water Treatment in Membrane Distillation [J]. Chemical Research in Chinese Universities, 2021, 37(3): 470-479.
[12]	LUO Yu, GONG Xiaoyan Shawn, XU Zhiwei, MENG Kai, ZHANG Ke-Qin, ZHAO Huijing. PTFE Electrospun Stent Graft——Preparation, Properties and Its Industrialization Prospect [J]. Chemical Research in Chinese Universities, 2021, 37(3): 589-597.
[13]	WANG Ruifang, LEI Weiwei, WANG Lei, LI Zhenyu, CHEN Jingyu, HU Zhenzhong. N-Doped Carbon Nanofibrous Film with Unique Wettability, Enhanced Supercapacitive Property, and Facile Capacity to Demulsify Surfactant Free Oil-in-water Emulsions [J]. Chemical Research in Chinese Universities, 2021, 37(3): 436-442.
[14]	LEI Chong, LI Wenzheng, WANG Gongwei, ZHUANG Lin, LU Juntao, XIAO Li. Improving the Catalytic Efficiency of NiFe-LDH/ATO by Air Plasma Treatment for Oxygen Evolution Reaction [J]. Chemical Research in Chinese Universities, 2021, 37(2): 293-297.
[15]	LUO Teng, HUANG Jianfeng, LIU Junmin. Application of Novel Calix[4]arene Metal-free Sensitizers in Dye-sensitized Photoelectrochemical Cells for Water Splitting [J]. Chemical Research in Chinese Universities, 2020, 36(6): 1091-1096.

Promotion Mechanism of H₂O for Stereoselectivity in Pd(II)-catalyzed C-H Arylation of Diarylphosphinamides with Arylboronic Acids

Knowledge

Abstract

Cite this article

share this article

References 14

Related Articles 15

Recommended Articles

Metrics

Comments