Halogenative Annulation Reactions of Alkyne-Tethered N- and O-Containing Arenes: Methods for Accessing Aryl-Fused Halogenated N- and O-Heterocycles

Jumreang Tummatorn; Somsak Ruchirawat; Charnsak Thongsornkleeb

doi:10.1055/a-2114-7582

Synthesis, Table of Contents

Synthesis 2023; 55(19): 3073-3089
DOI: 10.1055/a-2114-7582

short review

Special Issue Honoring Prof. Guoqiang Lin’s Contributions to Organic Chemistry

Halogenative Annulation Reactions of Alkyne-Tethered N- and O-Containing Arenes: Methods for Accessing Aryl-Fused Halogenated N- and O-Heterocycles

Authors

Jumreang Tummatorn

^aLaboratory of Medicinal Chemistry, Chulabhorn Research Institute, 54 Kamphaeng Phet 6, Laksi, Bangkok 10210, Thailand

^bProgram on Chemical Sciences, Chulabhorn Graduate Institute, Center of Excellence on Environmental Health and Toxicology (EHT), Office of Permanent Secretary (OPS), Ministry of Higher Education, Science, Research and Innovation (MHESI), 54 Kamphaeng Phet 6, Laksi, Bangkok 10210, Thailand
Somsak Ruchirawat

^aLaboratory of Medicinal Chemistry, Chulabhorn Research Institute, 54 Kamphaeng Phet 6, Laksi, Bangkok 10210, Thailand

^bProgram on Chemical Sciences, Chulabhorn Graduate Institute, Center of Excellence on Environmental Health and Toxicology (EHT), Office of Permanent Secretary (OPS), Ministry of Higher Education, Science, Research and Innovation (MHESI), 54 Kamphaeng Phet 6, Laksi, Bangkok 10210, Thailand
Charnsak Thongsornkleeb ∗

^aLaboratory of Medicinal Chemistry, Chulabhorn Research Institute, 54 Kamphaeng Phet 6, Laksi, Bangkok 10210, Thailand

^bProgram on Chemical Sciences, Chulabhorn Graduate Institute, Center of Excellence on Environmental Health and Toxicology (EHT), Office of Permanent Secretary (OPS), Ministry of Higher Education, Science, Research and Innovation (MHESI), 54 Kamphaeng Phet 6, Laksi, Bangkok 10210, Thailand

Abstract

All articles of this category

Dedicated to Prof. Guoqiang Lin’s contributions to organic chemistry

Abstract

Halogenative annulation of alkyne-tethered N- and O-containing arenes represents a general strategy for the construction of various halogenated N- and O-heterocycles. The methods employed are useful in producing valuable synthetic building blocks carrying C(sp²)–halide functional groups, which are useful synthetic handles, especially for cross-coupling reactions and a myriad of other transformations. When the alkyne is tethered to the heteroatom via an aromatic ring, the reaction gives rise to aryl-fused halogenated heterocycles. In this Short Review, various past and present halogenative annulation methods to construct aryl-fused halogenated N- and O-heterocycles are examined, with a focus on more recent technologies and the various roles of the participating halogenating agents. Additionally, future directions for this age-old, but still very useful, reaction are considered.

1 Introduction

2 Synthesis of Aryl-Fused Halogenated N-Heterocycles

2.1 Aryl-Fused Halogenated 5-Membered N-Heterocycles

2.2 Aryl-Fused Halogenated 6-Membered N-Heterocycles

2.3 Aryl-Fused Halogenated 7-Membered N-Heterocycles

3 Synthesis of Halogenated O-Heterocycles

3.1 Aryl-Fused Halogenated 5-Membered O-Heterocycles

3.2 Aryl-Fused Halogenated 6-Membered O-Heterocycles

3.3 Aryl-Fused Halogenated 7-Membered O-Heterocycles

4 Conclusion

Key words

alkynes - halogens - halogenative annulation - N-heterocycles - O-heterocycles - cyclization - halogenation

Full Text

References

References

1a Weix DJ. Acc. Chem. Res. 2015; 48: 1767
1b Laudadio G, Palkowitz MD, Ewing TE, Baran PS. ACS Med. Chem. Lett. 2022; 13: 1413
1c Perry IB, Brewer TF, Sarver PJ, Schultz DM, DiRocco DA, MacMillan DW. C. Nature 2018; 560: 70

2a Gabriele B, Mancuso R, Larock RC. Curr. Org. Chem. 2014; 18: 341
2b Aggarwal T, Kumar S, Verma AK. Org. Biomol. Chem. 2016; 14: 7639
2c China H, Kumar R, Kikushima K, Dohi T. Molecules 2020; 25: 6007

3 Yue D, Larock RC. Org. Lett. 2004; 6: 1037

4a Arcadi A, Pietropaolo E, Alvino A, Michelet V. Beilstein J. Org. Chem. 2014; 10: 449
4b Yang L, Ma Y, Song F, You J. Chem. Commun. 2014; 50: 3024

5a Hiroya K, Itoh S, Inamoto K, Shigehisa H, Sakamoto T. Heterocycles 2017; 95: 920
5b Yamashita M, Noro T, Iida A. Tetrahedron Lett. 2013; 54: 6848

6 Wei F, Wang X, Peng S, Jia Q, Jiang C, Liu S, Xu Z. Synthesis 2014; 46: 2168
7 Li Y.-L, Li J, Yu S.-N, Wang J.-B, Yu Y.-M, Deng J. Tetrahedron 2015; 71: 8271
8 Wu B, Wu J, Yoshikai N. Chem. Asian J. 2017; 12: 3123
9 Zhang J, Shi S.-Q, Hao W.-J, Dong G.-Y, Tu S.-J, Jiang B. J. Org. Chem. 2021; 86: 15886
10 Chen X, Zhang Z, Sun T, Cai H, Gao Y, Cai T, Shang T, Luo Y, Yu G, Shen H, Wu G, Hei Y, Li E, Fan G. Tetrahedron Lett. 2022; 90: 153614
11 Zhou C, Dubrovsky AV, Larock RC. J. Org. Chem. 2006; 71: 1626
12 Hessian KO, Flynn BL. Org. Lett. 2006; 8: 243
13 Deng S, Ouyang W, Bai J, Song X.-R, Yang R, Xiao Q. Synthesis 2021; 53: 2469
14 Lu H, Qiu Y.-C, Zhao Q, Tang R, Chen T, Hu L, Wu Z.-G. Tetrahedron Lett. 2022; 101: 153927
15 Likhar PR, Racharlawar SS, Karkhelikar MV, Subhas MS, Sridhar B. Synthesis 2011; 2407
16 Zhou Y, Zhang X, Zhang Y, Ruan L, Zhang J, Zhang-Negrerie D, Du Y. Org. Lett. 2017; 19: 150
17 Li X, Zhang B, Zhao B, Wang X, Xu L, Du Y. Adv. Synth. Catal. 2022; 364: 1427
18 Yaragorla S, Pareek A, Dada R, Saini PL. Eur. J. Org. Chem. 2017; 4600
19 Yaragorla S, Pareek A. Eur. J. Org. Chem. 2018; 1863
20 Rana M, Pareek A, Bhardwaj S, Arya G, Nimesh S, Arya H, Bhatt TK, Yaragorla S, Sharma AK. RSC Adv. 2020; 10: 28827
21 Cheng J, Zhai H, Bai J, Tang J, Lv L, Sun B. Tetrahedron Lett. 2014; 55: 4044
22 Yao T, Larock RC. J. Org. Chem. 2005; 70: 1432
23 Su H, Bao M, Huang J, Qiu L, Xu X. Adv. Synth. Catal. 2019; 361: 826
24 Rohokale RS, Kalshetti RG, Ramana CV. J. Org. Chem. 2019; 84: 2951
25 Naruto H, Togo H. Tetrahedron 2021; 83: 131993
26 Sie C.-Y, Chuang C.-P. Org. Biomol. Chem. 2018; 16: 5483
27 Yue D, Yao T, Larock RC. J. Org. Chem. 2005; 70: 10292
28 Volpe R, Aurelio L, Gillin MG, Krenske EH, Flynn BL. Chem. Eur. J. 2015; 21: 10191

29a Frota C, Rossini AF, Casagrande GA, Pizzuti L, Raminelli C. J. Braz. Chem. Soc. 2017; 28: 2038
29b Jung Y, Kim I. Org. Biomol. Chem. 2016; 14: 10454

30 Mehta S, Larock RC. J. Org. Chem. 2010; 75: 1652
31 Danilkina N, Kulyashova A, Khlebnikov A, Brase S, Balova I. J. Org. Chem. 2014; 79: 9018
32 Barluenga J, Alvarez-Pérez M, Rodríguez F, Fañanás FJ, Cuesta JA, García-Granda S. J. Org. Chem. 2003; 68: 6583
33 Okitsu T, Nakata K, Nishigaki K, Michioka N, Karatani M, Wada A. J. Org. Chem. 2014; 79: 5914
34 Wang W.-Y, Hu B.-L, Deng C.-L, Zhang X.-G. Tetrahedron Lett. 2014; 55: 1501
35 Sun Z, Xiang K, Tao H, Guo L, Li Y. Org. Biomol. Chem. 2018; 16: 6133
36 Sasaki T, Moriyama K, Togo H. Beilstein J. Org. Chem. 2018; 14: 345
37 Yan C.-Y, Wu Z.-W, He X.-Y, Ma Y.-H, Peng X.-R, Wang L, Yang Q.-Q. J. Org. Chem. 2023; 88: 647

38a Kong H, Li Q, Yin Y, Huang M, Kim JK, Zhu Y, Li Y, Wu Y. Org. Biomol. Chem. 2019; 17: 4621
38b Wu X, Jia M, Huang M, Kim JK, Zhao Z, Liu J, Xi J, Li Y, Wu Y. Org. Biomol. Chem. 2020; 18: 3346

39 Wang Z, Li X, Wang L, Li P. Tetrahedron 2019; 75: 1044
40 Tian J.-S, He Y, Gao Z.-Y, Liu X, Dong S.-F, Wu P, Loh T.-P. Org. Lett. 2021; 23: 6594
41 Pramanik M, Mathuri A, Sau S, Das M, Mal P. Org. Lett. 2021; 23: 8088
42 Huang B, Ma L, Qiu G. Tetrahedron Lett. 2017; 58: 2140
43 Shoji T, Tanaka M, Takagaki S, Miura K, Ohta A, Sekiguchi R, Ito S, Moric S, Okujima T. Org. Biomol. Chem. 2018; 16: 480
44 Luo J, He M, Chen P, Li J. Synth. Commun. 2018; 48: 1786
45 Kita Y, Yata T, Nishimoto Y, Chiba K, Yasuda M. Chem. Sci. 2018; 9: 6041
46 Habert L, Diachenko I, Retailleau P, Gillaizeau I. Org. Biomol. Chem. 2021; 19: 6623

47a Xing L, Zhang Y, Li B, Du Y. Org. Lett. 2019; 21: 1989
47b Norseeda K, Chaisan N, Thongsornkleeb C, Tummatorn J, Ruchirawat S. J. Org. Chem. 2019; 84: 16222

48 Kitamura T, Takachi T, Kawasato H, Taniguchi H. J. Chem. Soc., Perkin Trans. 1 1992; 1969