Recent Advances in the Pd-Catalyzed Coupling of Arylhydrazines and Ammonium Salts via C-N Bond Cleavage.

Tytuł:: Recent Advances in the Pd-Catalyzed Coupling of Arylhydrazines and Ammonium Salts via C-N Bond Cleavage.
Autorzy:: Tu Y; School of Pharmaceutical Sciences, Guangzhou Medical University, Guangzhou, Guangdong, 511436, China.; Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, D-52074, Aachen, Germany.
Zhao J; School of Pharmaceutical Sciences, Guangzhou Medical University, Guangzhou, Guangdong, 511436, China.
Źródło:: Chemical record (New York, N.Y.) [Chem Rec] 2021 Dec; Vol. 21 (12), pp. 3442-3457. Date of Electronic Publication: 2021 Jun 26.
Typ publikacji:: Journal Article; Review
Język:: English
Imprint Name(s):: Original Publication: New York : Wiley, c2000-
MeSH Terms:: Ammonium Compounds*
Palladium*
Alkynes ; Catalysis ; Salts
References:: .
A. F. Littke, G. C. Fu, Angew. Chem. 2002, 114, 4350-4386;.
Angew. Chem. Int. Ed. 2002, 41, 4176-4211;.
W. Shi, C. Liu, A. Lei, Chem. Soc. Rev. 2011, 40, 2761-2776;.
C. C. C. Johansson Seechurn, M. O. Kitching, T. J. Colacot, V. Snieckus, Angew. Chem. 2012, 124, 5150-5174;.
Angew. Chem. Int. Ed. 2012, 51, 5062-5085.
.
K. Zhao, L. Shen, Z. L. Shen, T. P. Loh, Chem. Soc. Rev. 2017, 46, 586-602;.
S. G. Modha, V. P. Mehta, E. V. Van der Eycken, Chem. Soc. Rev. 2013, 42, 5042-5055;.
N. Rodriguez, L. J. Goossen, Chem. Soc. Rev. 2011, 40, 5030-5048;.
I. P. Beletskaya, V. P. Ananikov, Chem. Rev. 2011, 111, 1596-1636;.
M. Oestreich, F. Tappe, V. Trepohl, Synthesis 2010, 18, 3037-3062.
A. Rudolph, M. Lautens, Angew. Chem. 2009, 121, 2694-2708;.
Angew. Chem. Int. Ed. 2009, 48, 2656-2670.
C. M. So, F. Y. Kwong, Chem. Soc. Rev. 2011, 40, 4963-4972.
F. Mo, G. Dong, Y. Zhang, J. Wang, Org. Biomol. Chem. 2013, 11, 1582-1593.
E. Erdik, Tetrahedron 1992, 48, 9577-9648.
W. Shi, C. Liu, A. Lei, Chem. Soc. Rev. 2011, 40, 2761-2776.
H. Shinokubo, K. Oshima, Eur. J. Org. Chem. 2004, 2081-2091.
M. Abdoli, H. Saeidian, J. Sulfur Chem. 2015, 36, 556-582.
.
J. Liu, S. Yuan, X. Song, G. Qiu, Chin. J. Org. Chem. 2016, 36, 1790-1796;.
A. Hosseinian, R. Mohammadi, S. Ahmadi, A. Monfared, Z. Rahmani, RSC Adv. 2018, 8, 33828-33844;.
S. Balgotra, P. K. Verma, R. A. Vishwakarma, S. D. Sawant, Catal. Rev. 2019, 62, 406-479;.
Z. X. Wang, B. Yang, Org. Biomol. Chem. 2020, 18, 1057-1072;.
G. Li, Y. Chen, J. Xia, Chin. J. Org. Chem. 2018, 38, 1949-1962.
B. Robinson, Chem. Rev. 1963, 63, 373-401.
M. K. Zhu, J. F. Zhao, T. P. Loh, Org. Lett. 2011, 13, 6308-6311.
Y. Bai, L. M. H. Kim, H. Liao, X.-W. Liu, J. Org. Chem. 2013, 78, 8821-8825.
J.-B. Liu, F.-J. Chen, N. Liu, J. Hu, RSC Adv. 2015, 5, 45843-45846.
J.-Q. Zhang, J. Cao, W. Li, S.-M. Li, Y.-K. Li, J.-T. Wang, L. Tang, New J. Chem. 2017, 41, 437-441.
J. B. Liu, H. Yan, H. X. Chen, Y. Luo, J. Weng, G. Lu, Chem. Commun. 2013, 49, 5268-5270.
J.-B. Liu, H.-P. Zhou, Y.-Y. Peng, Tetrahedron Lett. 2014, 55, 2872-2875.
Z. Peng, G. Hu, H. Qiao, P. Xu, Y. Gao, Y. Zhao, J. Org. Chem. 2014, 79, 2733-2738.
G. Wang, M. Meng, L. Deng, K. Cheng, C. Qi, Appl. Organomet. Chem. 2017, 32, e4203.
H. Zhang, C. Wang, Z. Li, Z. Wang, Tetrahedron Lett. 2015, 56, 5371-5376.
Y. Zhao, Q. Song, Chem. Commun. 2015, 51, 13272-13274.
Y. Chen, S. Guo, K. Li, J. Qu, H. Yuan, Q. Hua, B. Chen, Adv. Synth. Catal. 2013, 355, 711-715.
M. Li, Y. Ye, ChemCatChem 2015, 7, 4137-4142.
J. Cao, Z.-L. Chen, S.-M. Li, G.-F. Zhu, Y.-Y. Yang, C. Wang, W.-Z. Chen, J.-T. Wang, J.-Q. Zhang, L. Tang, Eur. J. Org. Chem. 2018, 2774-2779.
J.-B. Liu, L. Nie, H. Yan, L.-H. Jiang, J. Weng, G. Lu, Org. Biomol. Chem. 2013, 11, 8014-8017.
P. Chauhan, M. Ravi, S. Singh, K. S. R. Raju, V. Bajpai, B. Kumar, Wahajuddin, P. P. Yadav, RSC Adv. 2014, 4, 43336-43340.
P. Yao, Appl. Organomet. Chem. 2014, 28, 194-197.
W. Xu, G. Hu, P. Xu, Y. Gao, Y. Yin, Y. Zhao, Adv. Synth. Catal. 2014, 356, 2948-2954.
C. Wang, Z. Zhang, Y. Tu, Y. Li, J. Wu, J. Zhao, J. Org. Chem. 2018, 83, 2389-2394.
Y. Tu, Z. Zhang, T. Wang, J. Ke, J. Zhao, Org. Lett. 2017, 19, 3466-3469.
Y. Tu, L. Yuan, T. Wang, C. Wang, J. Ke, J. Zhao, J. Org. Chem. 2017, 82, 4970-4976.
K. Cheng, G. Wang, M. Meng, C. Qi, Org. Chem. Front. 2017, 4, 398-403.
X. Wang, Y. Huang, Y. Xu, X. Tang, W. Wu, H. Jiang, J. Org. Chem. 2017, 82, 2211-2218.
J. T. Reeves, D. R. Fandrick, Z. Tan, J. J. Song, H. Lee, N. K. Yee, C. H. Senanayake, Org. Lett. 2010, 12, 4388-4391.
Z. K. Yang, N. X. Xu, R. Takita, A. Muranaka, C. Wang, M. Uchiyama, Nat. Commun. 2018, 9, 1587-1593.
Z. K. Yang, D. Y. Wang, H. Minami, H. Ogawa, T. Ozaki, T. Saito, K. Miyamoto, C. Wang, M. Uchiyama, Chem. Eur. J. 2016, 22, 15693-15699.
Y. Kayashima, M. Komatsuda, K. Muto, J. Yamaguchi, Chem. Lett. 2020, 49, 836-839.
T. Wang, S. Yang, S. Xu, C. Han, G. Guo, J. Zhao, RSC Adv. 2017, 7, 15805-15808.
R. Phipps, P. Türtscher, H. Davis, Synthesis 2017, 50, 793-802.
H. J. Davis, M. T. Mihai, R. J. Phipps, J. Am. Chem. Soc. 2016, 138, 12759-12762.
Z. Zhang, H. Wang, N. Qiu, Y. Kong, W. Zeng, Y. Zhang, J. Zhao, J. Org. Chem. 2018, 83, 8710-8715.
T. Wang, J. Guo, X. Wang, H. Guo, D. Jia, H. Wang, L. Liu, RSC Adv. 2019, 9, 5738-5741.
L. Tang, Z. Y. Liu, W. She, C. Feng, Chem. Sci. 2019, 10, 8701-8705.
C. Han, Z. Zhang, S. Xu, K. Wang, K. Chen, J. Zhao, J. Org. Chem. 2019, 84, 16308-16313.
Q. Chen, F. Gao, H. Tang, M. Yao, Q. Zhao, Y. Shi, Y. Dang, C. Cao, ACS Catal. 2019, 9, 3730-3736.
L. Liu, W.-Q. Yu, T. Huang, T. Chen, Tetrahedron Lett. 2020, 61, 151647.
S. Xu, Z. Zhang, C. Han, W. Hu, T. Xiao, Y. Yuan, J. Zhao, J. Org. Chem. 2019, 84, 12192-12197.
F. Zhu, J. L. Tao, Z. X. Wang, Org. Lett. 2015, 17, 4926-4929.
W.-J. Pan, Z.-X. Wang, Asian J. Org. Chem. 2018, 7, 1626-1634.
H. Chen, H. Yang, N. Li, X. Xue, Z. He, Q. Zeng, Org. Process Res. Dev. 2019, 23, 1679-1685.
Y. N. Xu, M. Z. Zhu, Y. K. Lin, S. K. Tian, Org. Lett. 2019, 21, 7169-7173.
W. Yu, S. Yang, F. Xiong, T. Fan, Y. Feng, Y. Huang, J. Fu, T. Wang, Org. Biomol. Chem. 2018, 16, 3099-3103.
M. Miao, L.-L. Liao, G.-M. Cao, W.-J. Zhou, D.-G. Yu, Sci. China Chem. 2019, 62, 1519-1524.
F. Ye, Y. Ge, A. Spannenberg, H. Neumann, M. Beller, Nat. Commun. 2020, 11, 5383-5390.
L. M. Yang, S. S. Li, Y. Y. Zhang, J. L. Lu, J. T. Deng, A. J. Ma, X. Z. Zhang, S. Y. Zhang, J. B. Peng, Adv. Synth. Catal. 2021, 363, 1-6.
Grant Information:: 91853114, 21778025 National Natural Science Foundation of China
Contributed Indexing:: Keywords: C−N bond cleavage; ammonium salt; arylhydrazine; cross-coupling; palladium
Substance Nomenclature:: 0 (Alkynes)
0 (Ammonium Compounds)
0 (Salts)
5TWQ1V240M (Palladium)
Entry Date(s):: Date Created: 20210626 Date Completed: 20211229 Latest Revision: 20211229
Update Code:: 20240105
DOI:: 10.1002/tcr.202100089
PMID:: 34174146
: Czasopismo naukowe

Pełny tekst

Both arylhydrazines and quaternary ammonium salts are readily accessible or commercially available chemicals that show versatile reactivity in Pd-catalyzed coupling reactions via C-N bond cleavage. A tremendous array of coupling reactions involving reaction partners such as organoborons, aryl silanes, alkenes, alkynes, arylation or alkylation reagents in C-H functionalization and carbonylation reactions are summarized, in which arylhydrazines or quaternary ammonium salts function as aryl or alkyl donors. This account mainly focuses on recent advances in Pd-catalyzed coupling reactions with arylhydrazines or quaternary ammonium salts via C-N bond cleavage, including mechanistic elucidations.
(© 2021 The Chemical Society of Japan & Wiley-VCH GmbH.)

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