Palladium-Catalyzed Intermolecular Functionalization of Unactivated Methylene C(sp3)-H Bonds

doi:10.6023/cjoc202406012

Abstract

Although transition metal-catalyzed methylene C(sp³)-H functionalization is a great challenge, it has made noticeable progress in recent years. This review specifically describes Pd-catalyzed intermolecular functionalization of unactivated methylene C(sp³)-H bonds. A variety of reactions, including arylation, alkylation, alkenylation/alkynylation, acetoxylation, amination, halogenation, borylation, and silylation reactions, have been discussed in this review article. Due to the inert properties, methylene C(sp³)-H functionalization reaction usually rely on the use of directing group strategies, which can not only control regioselectivity but also address low reactivity issue. Various directing groups, including strongly coordinating bidentate auxiliaries and weakly coordinating innate functional groups, have proven to be eﬀective for enabling methylene C(sp³) -H functionalization.

Key words: palladium catalysis, C-H activation, methylene C(sp³)-H activation, cross-coupling

Cite this article

Mei Mingshun, Zhang Yanghui. Palladium-Catalyzed Intermolecular Functionalization of Unactivated Methylene C(sp³)-H Bonds[J]. Chinese Journal of Organic Chemistry, doi: 10.6023/cjoc202406012.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

References

[1] (a) Li B.-J.; Shi, Z.-J. Chem. Soc. Rev.2012, 41, 5588.
(b) Chu J. C. K.; Rovis, T. Angew. Chem. Int. Ed.2018, 57, 62.
(c) Chen Z.; Rong M.-Y.; Nie J.; Zhu X.-F.; Shi B.-F.; Ma, J.-A. Chem. Soc. Rev.2019, 48, 4921.
(d) Zhang Y.-H.; Shi G. - F.; Yu, J. -Q. In Comprehensive Organic Synthesis, 2nd ed.; Molander, G., Knochel, P., Eds.; Elsevier: Oxford U.K.,2014; Vol. 3, pp 1101.
[2] He J.; Wasa M.; Chan K. S. L.; Shao Q.; Yu J.-Q. Chem. Rev.2017, 117, 8754.
[3] (a) Herrmann, P.; Bach, T.Chem. Soc. Rev. 2011, 40, 2022.
(b) Dong, Z.; Ren, Z.; Thompson, S. J.; Xu, Y.; Dong, G.Chem. Rev. 2017, 117, 9333.
(c) Antermite, D.; Bull, J. A.Synthesis 2019, 51, 3171.
(d) Mishra, A. A.; Subhedar, D.; Bhanage, B. M. Chem. Rec. 2019, 19, 1829.
(e) Lucas, E. L.; Lam, N. Y. S.; Zhuang, Z.; Chan, H. S. S.; Strassfeld, D. A.; Yu, J.-Q.Acc. Chem. Res. 2022, 55, 537.
(f) Chen, X.; Li, B.; Tong, H.; Qi, L.; He, G.; Chen, G.Chin. J. Chem. 2022, 40, 2502.
(g) Wang P.-S.; Gong, L.-Z. Chin. J. Chem.2023, 41, 1841.
(h) Han Y. Q.; Shi, B.-F. Acta. Chimica. Sinica.2023, 81, 1522.
(i) Yoo, W.-J.; Li, C.-J. In C-H Activation, Yu, J.-Q.; Shi, Z., Eds. Springer Berlin Heidelberg: Berlin, Heidelberg, 2010; pp 281.
[4] (a) Wasa, M.; Engle, K. M.; Lin, D. W.; Yoo, E. J.; Yu, J.-Q.J. Am. Chem. Soc. 2011, 133, 19598.
(b) Xiao, K.-J.; Lin, D. W.; Miura, M.; Zhu, R.-Y.; Gong, W.; Wasa, M.;Yu, J.-Q.J. Am. Chem. Soc. 2014, 136, 8138.
(c) Chan, K. S. L.; Fu, H.-Y.; Yu, J.-Q.J. Am. Chem. Soc. 2015, 137, 2042.
(d) Wu Q.-F.; Wang X.-B.; Shen P.-X.; Yu J.-Q. ACS Catal.2018, 8, 2577.
(e) Shen P.-X.; Hu L.; Shao Q.; Hong K.; Yu, J.-Q. J. Am. Chem. Soc.2018, 140, 6545.
(f) Hu, L.; Shen, P.-X.; Shao, Q.; Hong, K.; Qiao, J. X.; Yu, J.-Q.Angew. Chem. Int. Ed. 2019, 58, 2134.
(g) Xiao, L.-J.; Hong, K.; Luo, F.; Hu, L.; Ewing, W. R.; Yeung, K.-S.; Yu, J.-Q.Angew. Chem. Int. Ed. 2020, 59, 9594.
(h) Zhuang, Z.; Yu, J.-Q.J. Am. Chem. Soc. 2020, 142, 12015.
[5] Campos, K. R.Chem. Soc. Rev. 2007, 36, 1069.
[6] (a) Zhang, F.-L.; Hong, K.; Li, T.-J.; Park, H.; Yu, J.-Q.Science 2016, 351, 252.
(b) Park, H.; Verma, P.; Hong, K.; Yu, J.-Q.Nat. Chem. 2018, 10, 755.
(c) Mei M.-S.; Zhang Y. Org. Lett.2023, 25, 4985.
[7] (a) Lyons T. W.; Sanford, M. S. Chem. Rev.2010, 110, 1147.
(b) Song G. Y.; Li, X. W. Acc. Chem. Res.2015, 48, 1007.
(c) He, G.; Wang, B.; Nack, W. A.; Chen, G.Acc. Chem. Res. 2016, 49, 635.
(d) Zhang, Q.; Shi, B.-F.Acc. Chem. Res. 2021, 54, 2750.
(e) Babu, S. A.; Aggarwal, Y.; Patel, P.; Tomar, R.Chem. Commun. 2022, 58, 2612.
(f) He Y.; Huang Z.; Wu K.; Ma J.; Zhou Y.-G.; Yu, Z. Chem. Soc. Rev.2022, 51, 2759.
(g) Das, J.; Ali, W.; Maiti, D.Trends in Chem. 2023, 5, 551.
(h) Yang X.; Liu X.; Wang, L. Chin. J. Org. Chem.2023, 43, 914.
[8] (a) Jin L.; Wang J.; Dong, G. Angew. Chem., Int. Ed.2018, 57, 12352
(b) Liu B.; Romine A. M.; Rubel C. Z.; Engle K. M.; Shi B.-F. Chem. Rev.2021, 121, 14957.
[9] Zaitsev V. G.; Shabashov D.; Daugulis, O. J. Am. Chem. Soc.2005, 127, 13154.
[10] Shabashov D.; Daugulis, O. J. Am. Chem. Soc.2010, 132, 3965.
[11] Reddy B. V. S.; Reddy L. R.; Corey, E. J. Org. Lett.2006, 8, 3391.
[12] Yan S.-B.; Zhang S.; Duan W.-L. Org. Lett.2015, 17, 2458.
[13] Tong H.-R.; Zheng S.; Li X.; Deng Z.; Wang H.; He G.; Peng Q.; Chen G. ACS Catal.2018, 8, 11502.
[14] Huang Y.; Lv X.; Tong H.-R.; He W.; Bai Z.; Wang H.; He G.; Chen G. Org. Lett.2024, 26, 94.
[15] Pan F.; Shen P.-X.; Zhang L.-S.; Wang X.; Shi Z.-J. Org. Lett.2013, 15, 4758.
[16] Gou Q.; Zhang Z.-F.; Liu Z.-C.; Qin, J. J. Org. Chem.2015, 80, 3176.
[17] (a) Ling P.-X.; Fang S.-L.; Yin X.-S.; Chen K.; Sun B.-Z.; Shi, B.-F. Chem. - Eur. J.2015, 21, 17503.
(b) Chen K.; Li Z.-W.; Shen P.-X.; Zhao H.-W.; Shi, Z.-J. Chem. - Eur. J.2015, 21, 7389.
[18] Li B.-J.; Shi, Z.-J. Adv. Synth. Catal.2016, 358, 887.
[19] Lou J.; Wang Q.; He Y.; Yu, Z. Adv. Synth. Catal.2018, 360, 4571.
[20] Yan S.-Y.; Han Y.-Q.; Yao Q.-J.; Nie X.-L.; Liu L.; Shi, B.-F. Angew. Chem. Int. Ed.2018, 57, 9093.
[21] Han Y.-Q.; Yang X.; Kong K.-X.; Deng Y.-T.; Wu L.-S.; Ding Y.; Shi, B.-F. Angew. Chem. Int. Ed.2020, 59, 20455.
[22] Zhu R.-Y.; Liu L.-Y.; Park H. S.; Hong K.; Wu Y.; Senanayake C. H.; Yu, J.-Q. J. Am. Chem. Soc.2017, 139, 16080.
[23] Xia G.; Weng J.; Liu L.; Verma P.; Li Z.; Yu J.-Q. Nat. Chem.2019, 11, 571.
[24] Antermite D.; White A. J. P.; Casarrubios L.; Bull, J. A. ACS Catal.2018, 8, 7781.
[25] He G.; Chen, G. Angew. Chem. Int. Ed.2011, 50, 5192.
[26] Zhang Y.-F.; Zhao H.-W.; Wang H.; Wei J.-B.; Shi, Z.-J. Angew. Chem. Int. Ed.2015, 54, 13686.
[27] (a) Gandeepan, P.; Ackermann, L.Chem 2018, 4, 199.
(b) Higham J. I.; Bull, J. A. Org. Biomol. Chem.2020, 18, 7291.
(c) Goswami N.; Bhattacharya T.; Maiti, D. Nat. Rev. Chem.2021, 5, 646.
[28] Yang K.; Li Q.; Liu Y.; Li G.; Ge, H. J. Am. Chem. Soc.2016, 138, 12775.
[29] Li Y.-H.; Ouyang Y.; Chekshin N.; Yu, J.-Q. J. Am. Chem. Soc.2022, 144, 4727.
[30] St John-Campbell S.; White A. J. P.; Bull, J. A. Org. Lett.2020, 22, 1807.
[31] Hong K.; Park H.; Yu J.-Q. ACS Catal.2017, 7, 6938.
[32] Pan L.; Yang K.; Li G.; Ge H. Chem. Commun.2018, 54, 2759.
[33] Wang J.; Dong C.; Wu L.; Xu M.; Lin J.; Wei, K. Adv. Synth. Catal.2018, 360 3709.
[34] (a) Dong, C.; Wu, L.; Yao, J.; Wei, K.Org. Lett. 2019, 21, 2085.
(b) Cheng Y.; Zheng J.; Tian C.; He Y.; Zhang C.; Tan Q.; An G.; Li, G. Asian J. Org. Chem.2019, 8, 526.
[35] Xu Y.; Young M. C.; Wang C.; Magness D. M.; Dong, G. Angew. Chem. Int. Ed.2016, 55, 9084.
[36] Wu Y.; Chen Y.-Q.; Liu T.; Eastgate M. D.; Yu, J.-Q. J. Am. Chem. Soc.2016, 138, 14554.
[37] Yada A.; Liao W.; Sato Y.; Murakami, M. Angew. Chem. Int. Ed.2017, 56, 1073.
[38] Shabashov D.; Daugulis O. Org. Lett.2005, 7, 3657.
[39] Le K. K. A.; Nguyen H.; Daugulis, O. J. Am. Chem. Soc.2019, 141, 37, 14728.
[40] Wu, K.; Lam, N.; Strassfeld, D. A.; Fan, Z.; Qiao, J. X.; Liu, T.; Stamos, D.; Yu, J.-Q.Angew. Chem. Int. Ed. 2024, 63, e202400509.
[41] Wasa M.; Chan K. S. L.; Zhang X.-G.; He J.; Miura M.; Yu, J.-Q. J. Am. Chem. Soc.2012, 134, 18570.
[42] (a) Chen G.; Gong W.; Zhuang Z.; Andä M. S.; Chen Y.-Q.; Hong X.; Yang Y.-F.; Liu T.; Houk K. N.; Yu J.-Q. Science2016, 353, 1023.
(b) Hill D. E.; Pei Q.-l.; Zhang E.-x.; Gage J. R.; Yu J.-Q.; Blackmond, D. G. ACS Catal.2018, 8, 1528.
[43] Shang M.; Feu K. S.; Vantourout J. C.; Barton L. M.; Osswald H. L.; Kato N.; Gagaring K.; McNamara C. W.; Chen G.; Hu L.; Ni S.; Fernndez-Canelas P.; Chen M.; Merchant R. R.; Qin T.; Schreiber S. L.; Melillo B.; Yu J.-Q.; Baran, P. S. Proc. Natl. Acad. Sci. U. S. A.2019, 116, 8721.
[44] Andrä M. S.; Schifferer L.; Pollok C. H.; Merten C.; Gooßen L. J.; Yu, J.-Q. Chem. Eur. J.2019, 25, 8503.
[45] Topczewski J. J.; Cabrera P. J.; Saper N. I.; Sanford M. S. Nature2016,531, 220.
[46] Cabrera P. J.; Lee M.; Sanford, M. S. J. Am. Chem. Soc.2018, 140, 5599.
[47] Kapoor M.; Liu D.; Young, M. C. J. Am. Chem. Soc.2018, 140, 6818.
[48] (a) Font M.; Quibell J. M.; Perry G. J. P.; Larrosa I. Chem. Commun.2017, 53, 5584.
(b) He C.; Whitehurst W. G.; Gaunt M. J. Chem2019, 5, 1031.
(c) He, C.; Zu, B.; Guo, Y.; Ke, J. Synthesis 2021, 53, 2029.
(d) Das J.; Mal D. K.; Maji S.; Maiti D. ACS Catal.2021, 11, 4205.
[49] Hu, L.; Meng, G.; Yu, J.-Q.J. Am. Chem. Soc. 2022, 144, 20550.
[50] Yang J.-M.; Lin Y.-K.; Sheng T.; Hu L.; Cai X.-P.; Yu J.-Q. Science2023, 380, 639.
[51] Kang, G.; Strassfeld, D. A.; Sheng, T.; Chen, C.-Y.; Yu, J.-Q.Nature 2023, 618, 519.
[52] Zhang, T.; Zhang, Z.-Y.; Kang, G.; Sheng, T.; Yan, J.-L.; Yang, Y.-B.; Ouyang, Y.; Yu, J.-Q.Science 2024, 384, 793.
[53] Hoque M. E.; Yu, J.-Q. Angew. Chem. Int. Ed.2023, 62, e202312331.
[54] Strassfeld D. A.; Chen C.-Y.; Park H. S.; Phan D. Q.; Yu J.-Q. Nature2023, 622, 80.
[55] Chen K.; Hu F.; Zhang S.-Q.; Shi B.-F. Chem. Sci.2013, 4, 3906.
[56] Zhang, S.-Y.; He, G.; Nack, W. A.; Zhao, Y.; Li, Q.; Chen, G.J. Am. Chem. Soc. 2013, 135, 2124.
[57] Liu Y.; Yang K.; Ge H. Chem. Sci.2016, 7, 2804.
[58] He G.; Chen, G. Angew. Chem. Int. Ed.2011, 50, 5192.
[59] Zhang Y.-F.; Zhao H.-W.; Wang H.; Wei J.-B.; Shi, Z.-J. Angew. Chem. Int. Ed.2015, 54, 13686.
[60] Ding Y.; Han Y.-Q.; Wu L.-S.; Zhou T.; Yao Q.-J.; Feng Y.-L.; Li Y.; Kong K.-X.; Shi, B.-F. Angew. Chem. Int. Ed.2020, 59, 14060.
[61] Liu, Y.; Wang, Y.; Dai, W.; Huang, W.; Li, Y.; Liu, H.Angew. Chem. Int. Ed. 2020, 59, 3491.
[62] Wu J.; Kaplaneris N.; Ni S.; Kaltenhäuser F.; Ackermann L. Chem. Sci.2020, 11, 6521.
[63] Gadde K.; Bheemireddy N. R.; Heitkämper J.; Nova A.; Maes, B. U. W. ACS Catal.2024, 14, 1157.
[64] Ano Y.; Tobisu M.; Chatani, N. J. Am. Chem. Soc.2011,133, 12984.
[65] Landge V. G.; Parveen A.; Nandakumar A.; Balaraman E. Chem. Commun.2018, 54, 7483.
[66] Han, Y.-Q.; Ding, Y.; Zhou, T.; Yan, S.-Y.; Song, H.; Shi, B.-F.J. Am. Chem. Soc. 2019, 141, 4558.
[67] Cabrera-Pardo J. R.; Trowbridge A.; Nappi M.; Ozaki K.; Gaunt, M. J. Angew. Chem., Int. Ed.2017, 56, 11958.
[68] Hogg K. F.; Trowbridge A.; Alvarez-Pérez A.; Gaunt, M. J. Chem. Sci.2017, 8, 8198.
[69] Desai L. V.; Hull K. L.; Sanford, M. S. J. Am. Chem. Soc.2004, 126, 9542.
[70] Reddy B. V. S.; Reddy L. R.; Corey, E. J. Org. Lett.2006, 8, 3391.
[71] Ren Z.; Mo F.; Dong, G. J. Am. Chem. Soc.2012, 134, 16991.
[72] Chen K.; Zhang S.-Q.; Jiang H.-Z.; Xu J.-W.; Shi, B.-F. Chem. Eur. J.2015, 21, 3264.
[73] Shan G.; Yang X.; Zong Y.; Rao, Y. Angew. Chem. Int. Ed.2013, 52, 13606.
[74] Chen, F.-J.; Zhao, S.; Hu, F.; Chen, K.; Zhang, Q.; Zhang, S.-Q.; Shi, B.-F.Chem. Sci. 2013, 4, 4187.
[75] Bai, H.-Y.; Ma, Z.-G.; Yi, M.; Lin, J.-B.; Zhang, S.-Y.ACS Catal. 2017, 7, 2042.
[76] Zhu R.-Y.; Tanaka K.; Li G.-C.; He J.; Fu H.-Y.; Li S.-H.; Yu, J.-Q. J. Am. Chem. Soc.2015, 137, 7067.
[77] Zhang Q.; Yin X.-S.; Chen K.; Zhang S.-Q.; Shi, B.-F. J. Am. Chem. Soc.2015, 137, 8219.
[78] Mao Y.-J.; Lou S.-J.; Hao H.-Y.; Xu, D.-Q. Angew. Chem. Int. Ed.2018, 57, 14085.
[79] Chen Y.-Q.; Singh S.; Wu Y.; Wang Z.; Hao W.; Verma P.; Qiao J. X.; Sunoj R. B.; Yu, J.-Q. J. Am. Chem. Soc.2020, 142, 9966.
[80] He J.; Shao Q.; Wu Q.; Yu, J.-Q. J. Am. Chem. Soc.2017, 139, 3344.
[81] Kanyiva, K. S.; Kuninobu, Y.; Kanai, M.Org. Lett. 2014, 16, 1968.
[82] Pan J.-L.; Li Q.-Z.; Zhang T.-Y.; Hou S.-H.; Kang J.-C.; Zhang S.-Y. Chem. Commun.2016, 52, 13151.
[83] Vyhivskyi, O.; Kudashev, A.; Miyakoshi, T.; Baudoin, O.Chem. Eur. J. 2021, 27, 1231
[84] Zhang Z.; Wei F.; Wang X.; Zhang Y. Org. Lett.2024, 26, 3586.
[85] Uttry A.; Mal S.; van Gemmeren, M. J. Am. Chem. Soc.2021, 143, 10895.
[86] Watanabe A.; Hama K.; Watanabe K.; Fujiwara Y.; Yokoyama K.; Murata S.; Takita, R. Angew. Chem. Int. Ed.2022, 61, e202202779.
[87] Wang X.; Sun Z.; Li T.; Perveen S.; Li P. Green Chem.2024, 26, 3767.

钯催化惰性亚甲基C(sp³)-H键分子间官能团化反应

Palladium-Catalyzed Intermolecular Functionalization of Unactivated Methylene C(sp³)-H Bonds

PDF

Knowledge

Abstract

Cite this article

share this article

References

Related Articles 15

Recommended Articles

Metrics

Comments

[1]	Wenjuan Liu, Pinhong Chen. Palladium-Catalyzed Cyclization of 1,6-Enynes [J]. Chinese Journal of Organic Chemistry, 2024, 44(7): 2077-2091.
[2]	Mengke Wen, Yiyue Li, Haokang Du, Zhangpei Chen, Xifa Yang. Synthesis of Spiropyrans via Rh(III)-Catalyzed [3+3] Cyclization of 3-Aryl-2H-1,4-benzoxazine and Diazonaphthalene-2H-ones [J]. Chinese Journal of Organic Chemistry, 2024, 44(7): 2223-2232.
[3]	Qian Zhang, Yaolu Ying, Hongyin Zhang, Linbo Xu, Xinkui Lin, Xiaolei Huang. Palladium-Catalyzed Reductive Cross-Coupling of Propargyl Acetates with Aryl Iodides Involving the Insertion of SO₂ [J]. Chinese Journal of Organic Chemistry, 2024, 44(6): 2033-2040.
[4]	Lei Yu, Kang Sheng, Ting Li, Conghui Tang. Heterogeneous Iron-Catalyzed Oxyalkylation of Vinylarenes via C(sp³)—H Activation of Cyclic Ethers [J]. Chinese Journal of Organic Chemistry, 2024, 44(6): 1978-1986.
[5]	Yuxuan Yan, Wanqing Lu, Huijun Qian, Leiyang Lv, Zhiping Li. Pd-Catalyzed Ring-Opening of gem-Difluorocyclopropanes for the Mono- and Bis-fluoroallylation of 1,3-Dicarbonyls [J]. Chinese Journal of Organic Chemistry, 2024, 44(5): 1630-1640.
[6]	Donghong Luo, Ping Li, Zhicai Chen, Jiayi Yang, Mengfan Sun, Juyou Lu. Pd-Catalyzed Cross-Coupling of o-Carboranyl Pyridyl Halides: Synthesis of o-Carboranyl Biaryls, Aminopyridines and Alkynylpyridine Derivatives [J]. Chinese Journal of Organic Chemistry, 2024, 44(5): 1568-1575.
[7]	Junjun Liu, Taotao Lu, Ping Ma, Qingyang Zhao, Fuk Yee Kwong. Palladium-Catalyzed C(sp³)—Si Bonds Transformation for Construct-ing Trifluoropropyl (Hetero)arenes through C(sp³)—C(sp²) Cross-Coupling Reactions [J]. Chinese Journal of Organic Chemistry, 2024, 44(4): 1319-1326.
[8]	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.
[9]	Hong'en Tong, Hongyu Guo, Rong Zhou. Progress on Visible-Light Promoted Addition Reactions of Inert C—H Bonds to Carbonyls [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 54-69.
[10]	Yixin Jiang, Boxiao Tang, Haibo Mao, Xuexia Chen, Yangjie Yu, Cuiying Quan, Zhaoyang Xu, Jinhui Shi, Yilin Liu. A Green, Recyclable and Carrier-Free Study for the Coupling Reaction of Alkenes with Aryl Iodides in H₂O-Polyethylene Glycol (PEG-200) [J]. Chinese Journal of Organic Chemistry, 2023, 43(9): 3210-3215.
[11]	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.
[12]	Yuchao Wang, Jinbiao Liu, Zhitao He. Palladium-Catalyzed Asymmetric Hydrofunctionalizations of Conjugated Dienes [J]. Chinese Journal of Organic Chemistry, 2023, 43(8): 2614-2627.
[13]	Yuxing Tong, Ziwei Wang, Ben Liu, Yaowei Xu, Song Gao, Xiangbing Tang, Xinghua Zhang. Recent Advances in Synthesis of 3-Sulfenylated Indoles [J]. Chinese Journal of Organic Chemistry, 2023, 43(4): 1310-1324.
[14]	Xun Xiang, Zhaolin He, Xiuqin Dong. Recent Advances of Efficient Synthesis of Chiral Molecules Promoted by Pd/Chiral Phosphoric Acid Synergistic Catalysis [J]. Chinese Journal of Organic Chemistry, 2023, 43(3): 791-808.
[15]	Biao Ma, Miaomiao Zhang, Zhanyu Li, Jinsong Peng, Chunxia Chen. Recent Advance of Transition Metal-Free Catalyzed Suzuki-Type Cross Coupling Reaction [J]. Chinese Journal of Organic Chemistry, 2023, 43(2): 455-470.

钯催化惰性亚甲基C(sp3)-H键分子间官能团化反应