Remote-Carbonyl-Directed Consecutive Arylation of Terminal Alkenes for the Synthesis of Tetrasubstituted Olefins

Kun Li; Runze Luan; Yu Du; Weiping Su

doi:10.1055/a-2323-0633

Synthesis, Table of Contents

Synthesis 2024; 56(13): 1989-1998
DOI: 10.1055/a-2323-0633

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Remote-Carbonyl-Directed Consecutive Arylation of Terminal Alkenes for the Synthesis of Tetrasubstituted Olefins

Kun Li

^aCollege of Chemistry & Materials Science, Fujian Normal University, Fuzhou 350007, P. R. of China

^bState Key Laboratory of Structural Chemistry, Fujian Institute of Research on the Structure of Matter, Chinese Academy of Sciences, 155 Yangqiao Road West, Fuzhou 350002, P. R. of China

,

Runze Luan

^bState Key Laboratory of Structural Chemistry, Fujian Institute of Research on the Structure of Matter, Chinese Academy of Sciences, 155 Yangqiao Road West, Fuzhou 350002, P. R. of China

,

Yu Du ∗

^aCollege of Chemistry & Materials Science, Fujian Normal University, Fuzhou 350007, P. R. of China

^bState Key Laboratory of Structural Chemistry, Fujian Institute of Research on the Structure of Matter, Chinese Academy of Sciences, 155 Yangqiao Road West, Fuzhou 350002, P. R. of China

^cFujian Science and Technology Innovation Laboratory for Optoelectronic Information of China, Fuzhou 350108, P. R. of China

,

Weiping Su∗

^aCollege of Chemistry & Materials Science, Fujian Normal University, Fuzhou 350007, P. R. of China

^bState Key Laboratory of Structural Chemistry, Fujian Institute of Research on the Structure of Matter, Chinese Academy of Sciences, 155 Yangqiao Road West, Fuzhou 350002, P. R. of China

^cFujian Science and Technology Innovation Laboratory for Optoelectronic Information of China, Fuzhou 350108, P. R. of China

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Abstract

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Abstract

The highly efficient synthesis of all-carbon tetrasubstituted olefins has been a challenge for decades, especially of multi-aryl-substituted olefins which are widely used in functional organic materials and pharmaceuticals. This work presents a carbonyl-directed palladium-catalyzed consecutive arylation of terminal alkenes with aryl iodides under mild conditions, in which a series of triarylated tetrasubstituted olefins were obtained in moderate yields. Because a weak chelation effect is generally difficult to support such a thorough trifold Heck arylation, and β-trans-selective alkenyl C–H activation cannot be achieved via a twisted endo-metallocyclic intermediate, the key to success is the compatibility between several mechanisms, including Heck reaction, C–H activation and E/Z-isomerization. Here, the judicious selection of a flexible-alkyl-chain-tethered carbonyl group seems to be critical, as it provides a proper chelation effect that not only assists distal alkenyl functionalization or isomerization, but also avoids byproducts caused by other possible β-H elimination or migration. The strategy developed herein greatly streamlines the preparation of the target molecules, and the protocol covers a range of readily available terminal alkenes bearing a native directing group (i.e., aldehyde, ketone and ester) and aryl iodides.

Key words

carbonyl-directed - consecutive arylation - E/Z-isomerization - all-carbon tetrasubstituted olefins - alkenyl C–H activation - Mizoroki–Heck reaction

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References

References

1a Kwok RT. K, Leung CW. T, Lam JW. Y, Tang BZ. Chem. Soc. Rev. 2015; 44: 4228
1b Tandon N, Luxami V, Tandon R, Paul K. Asian J. Org. Chem. 2020; 9: 1432

2a Daik R, Feast WJ, Batsanov AS, Howard JA. K. New J. Chem. 1998; 22: 1047
2b Moonen NN. P, Boudon C, Gisselbrecht J.-P, Seiler P, Gross M, Diederich F. Angew. Chem. Int. Ed. 2002; 41: 3044
2c Cerda-García-Rojas CM, Coronel Adel C, de Lampasona ME. P, Catalán CA. N, Joseph-Nathan P. J. Nat. Prod. 2005; 68: 659

3 Flynn AB, Ogilvie WW. Chem. Rev. 2007; 107: 4698

4a Liu W, Kong W. Org. Chem. Front. 2020; 7: 3941
4b Düfert A, Werz DB. Chem. Eur. J. 2016; 22: 16718

Some recent examples of all-carbon tetrasubstituted olefin synthesis via alkynyl or propadienyl carbometalation:

5a Dutta S, Shandilya S, Yang S, Gogoi MP, Gandon V, Sahoo AK. Nat. Commun. 2022; 13: 1360
5b Zhan Y.-Z, Xiao N, Shu W. Nat. Commun. 2021; 12: 928
5c Wisthoff MF, Pawley SB, Cinderella AP, Watson DA. J. Am. Chem. Soc. 2020; 142: 12051
5d Lv W, Liu S, Chen Y, Wen S, Lan Y, Cheng G. ACS Catal. 2020; 10: 10516
5e Reding A, Jones PG, Werz DB. Angew. Chem. Int. Ed. 2018; 57: 10610
5f Yoon H, Rölz M, Landau F, Lautens M. Angew. Chem. Int. Ed. 2017; 56: 10920
5g Milde B, Reding A, Geffers FJ, Jones PG, Werz DB. Chem. Eur. J. 2016; 22: 14544
5h Itoh T, Shimizu Y, Kanai M. J. Am. Chem. Soc. 2016; 138: 7528
5i Dai J, Wang M, Chai G, Fu C, Ma S. J. Am. Chem. Soc. 2016; 138: 2532
5j Evans PA, Negru DE, Shang D. Angew. Chem. Int. Ed. 2015; 54: 4768

Some reviews on chelation-assisted Mizoroki–Heck reactions:

6a Nakashima Y, Hirata G, Sheppard TD, Nishikata T. Asian J. Org. Chem. 2020; 9: 480
6b Oestreich M. Top. Organomet. Chem. 2007; 24: 169
6c Oestreich M. Eur. J. Org. Chem. 2005; 783

Some recent examples of chelation-assisted Mizoroki–Heck reactions:

7a Zhao Y, Wang S, Shao H, Tan X, Chen R, Loh T.-P, Zhou JS, Wu X. Org. Lett. 2023; 25: 4258
7b Tsai S.-Y, Huang Y.-W, Chou C.-M. Adv. Synth. Catal. 2023; 365: 699
7c Jiang K, Wang H, Xie Y, Jiang H, Lei M, Yin B. ACS Catal. 2023; 13: 3520
7d Zhu B, Li Z, Chen F, Xiong W, Tan X, Lei M, Wu W, Jiang H. Chem. Commun. 2022; 58: 12688
7e Lin C, Chen S, Wang Y, Gao F, Shen L. Org. Chem. Front. 2022; 9: 608
7f Tsai J.-J, Huang Y.-H, Chou C.-M. Org. Lett. 2021; 23: 9468
7g Yang S, Liu L, Zhou Z, Huang Z, Zhao Y. Org. Lett. 2021; 23: 296
7h Landge VG, Maxwell JM, Chand-Thakuri P, Kapoor M, Diemler ET, Young MC. JACS Au 2021; 1: 13
7i de Oliveira VC, de Oliveira JM, Menezes da Silva VH, Khan IU, Correia CR. D. Adv. Synth. Catal. 2020; 362: 3395
7j Ke L, Chen Z. Commun. Chem. 2020; 3: 48
7k Romine AM, Yang KS, Karunananda MK, Chen JS, Engle KM. ACS Catal. 2019; 9: 7626
7l Huffman TR, Wu Y, Emmerich A, Shenvi RA. Angew. Chem. Int. Ed. 2019; 58: 2371
7m Tang J, Hackenberger D, Goossen LJ. Angew. Chem. Int. Ed. 2016; 55: 11296

Chelation-assisted all-carbon tetrasubstituted olefin synthesis via Heck arylation:

8a Lee HS, Kim KH, Kim SH, Kim JN. Adv. Synth. Catal. 2012; 354: 2419
8b Itami K, Mineno M, Muraoka N, Yoshida J. J. Am. Chem. Soc. 2004; 126: 11778
8c Itami K, Nokami T, Ishimura Y, Mitsudo K, Kamei T, Yoshida J. J. Am. Chem. Soc. 2001; 123: 11577
8d Nilsson P, Larhed M, Hallberg A. J. Am. Chem. Soc. 2001; 123: 8217

9 Larhed M, Andersson C.-M, Hallberg A. Tetrahedron 1994; 50: 285

Some reviews on chelation-assisted alkenyl C–H functionalization:

10a Wang Y, Zhu Y, Xu L, He R, Zhang J. Chin. J. Org. Chem. 2022; 42: 2000
10b Zhang J, Lu X, Shen C, Xu L, Ding L, Zhong G. Chem. Soc. Rev. 2021; 50: 3263
10c Wang K, Hu F, Zhang Y, Wang J. Sci. China: Chem. 2015; 58: 1252

Some recent examples of geminal group directed alkenyl C–H functionalization:

11a Shen C, Zhu Y, Jin S, Xu K, Luo S, Xu L, Zhong G, Zhong L, Zhang J. Org. Chem. Front. 2022; 9: 989
11b Schreib BS, Son M, Aouane FA, Baik M.-H, Carreira EM. J. Am. Chem. Soc. 2021; 143: 21705
11c Schreib BS, Fadel M, Carreira EM. Angew. Chem. Int. Ed. 2020; 59: 7818
11d Xu S, Hirano K, Miura M. Org. Lett. 2020; 22: 9059
11e Han B, Li B, Qi L, Yang P, He G, Chen G. Org. Lett. 2020; 22: 6879
11f Schreib BS, Carreira EM. J. Am. Chem. Soc. 2019; 141: 8758
11g Meng K, Li T, Yu C, Shen C, Zhang J, Zhong G. Nat. Commun. 2019; 10: 5109

Some recent examples of vicinal group directed alkenyl C–H functionalization:

12a Wang S.-G, Liu Y, Cramer N. Angew. Chem. Int. Ed. 2019; 58: 18136
12b Yang Q.-L, Xing Y.-K, Wang X.-Y, Ma H.-X, Weng X.-J, Yang X, Guo H.-M, Mei T.-S. J. Am. Chem. Soc. 2019; 141: 18970
12c Sun Y, Meng K, Zhang J, Jin M, Huang N, Zhong G. Org. Lett. 2019; 21: 4868
12d Xu L, Meng K, Zhang J, Sun Y, Lu X, Li T, Jiang Y, Zhong G. Chem. Commun. 2019; 55: 9757
12e Luo Y.-C, Yang C, Qiu S.-Q, Liang Q.-J, Xu Y.-H, Loh T.-P. ACS Catal. 2019; 9: 4271
12f Wu X, Ji H. J. Org. Chem. 2018; 83: 12094
12g Tan E, Quinonero O, Elena de Orbe M, Echavarren AM. ACS Catal. 2018; 8: 2166
12h Yu C, Zhang J, Zhong G. Chem. Commun. 2017; 53: 9902
12i Shankar M, Guntreddi T, Ramesh E, Sahoo AK. Org. Lett. 2017; 19: 5665
12j Zhu Y.-Q, Liu Y, Wang H, Liu W, Li C.-J. Org. Chem. Front. 2016; 3: 971
12k Jiang Q, Guo T, Wu K, Yu Z. Chem. Commun. 2016; 52: 2913
12l Casanova N, Del Rio KP, García-Fandiño R, Mascareñas JL, Gulías M. ACS Catal. 2016; 6: 3349
12m Zhou Z, Liu G, Lu X. Org. Lett. 2016; 18: 5668
12n Zell D, Warratz S, Gelman D, Garden SJ, Ackermann L. Chem. Eur. J. 2016; 22: 1248
12o Zhou B, Hu Y, Wang C. Angew. Chem. Int. Ed. 2015; 54: 13659

13 Wu Z, Fatuzzo N, Dong G. J. Am. Chem. Soc. 2020; 142: 2715

Some examples of the synthesis of all-carbon tetrasubstituted olefins via chelation-assisted alkenyl C–H activation:

14a Jiang B, Zhao M, Li S.-S, Xu Y.-H, Loh T.-P. Angew. Chem. Int. Ed. 2018; 57: 555
14b Hu X.-H, Zhang J, Yang X.-F, Xu Y.-H, Loh T.-P. J. Am. Chem. Soc. 2015; 137: 3169
14c Ilies L, Matsubara T, Ichikawa S, Asako S, Nakamura E. J. Am. Chem. Soc. 2014; 136: 13126
14d Wang H, Beiring B, Yu D.-G, Collins KD, Glorius F. Angew. Chem. Int. Ed. 2013; 52: 12430
14e Hou W, Zhou B, Yang Y, Feng H, Li Y. Org. Lett. 2013; 15: 1814
14f Li Y, Zhang X.-S, Zhu Q.-L, Shi Z.-J. Org. Lett. 2012; 14: 4498
14g Kuninobu Y, Nishina Y, Matsuki T, Takai K. J. Am. Chem. Soc. 2008; 130: 14062

15 Luan R, Lin P, Li K, Du Y, Su W. Nat. Commun. 2024; 15: 1723
16 Matsuura R, Karunananda MK, Liu M, Nguyen N, Blackmond DG, Engle KM. ACS Catal. 2021; 11: 4239
17 Kudo E, Sasaki K, Kawamata S, Yamamoto K, Murahashi T. Nat. Commun. 2021; 12: 1473

18a Liu Z, Li X, Zeng T, Engle KM. ACS Catal. 2019; 9: 3260
18b Bai Z, Zheng S, Bai Z, Song F, Wang H, Peng Q, Chen G, He G. ACS Catal. 2019; 9: 6502
18c Wang H, Bai Z, Jiao T, Deng Z, Tong H, He G, Peng Q, Chen G. J. Am. Chem. Soc. 2018; 140: 3542
18d Liu M, Yang P, Karunananda MK, Wang Y, Liu P, Engle KM. J. Am. Chem. Soc. 2018; 140: 5805

19 Bhattacharya T, Ghosh A, Maiti D. Chem. Sci. 2021; 12: 3857
20 Kaku K, Ravindra MP, Tong N, Choudhary S, Li X, Yu J, Karim M, Brzezinski M, O’Connor C, Hou Z, Matherly LH, Gangjee A. ACS Med. Chem. Lett. 2023; 14: 1682

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