Acetate/Alkoxide/Halide Shuttle Systems Mediated by Lewis Acid Catalysts for Insertion Reaction of a One-Carbon Unit into Carbon–Carbon or Carbon–Halogen Bonds

Yoshihiro Nishimoto; Makoto Yasuda

doi:10.1055/a-2136-3609

Synlett, Table of Contents

Synlett 2024; 35(04): 367-378
DOI: 10.1055/a-2136-3609

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11th Singapore International Chemistry Conference (SICC-11)

Acetate/Alkoxide/Halide Shuttle Systems Mediated by Lewis Acid Catalysts for Insertion Reaction of a One-Carbon Unit into Carbon–Carbon or Carbon–Halogen Bonds

Yoshihiro Nishimoto ∗

^aDepartment of Applied Chemistry, Graduate School of Engineering, Osaka University, 2-1 Yamadaoka, Suita, Osaka 565-0871, Japan

^bInnovative Catalysis Science Division, Institute for Open and Transdisciplinary Research Initiatives (ICS-OTRI), Osaka University, Suita, Osaka 565-0871, Japan

,

Makoto Yasuda ∗

^aDepartment of Applied Chemistry, Graduate School of Engineering, Osaka University, 2-1 Yamadaoka, Suita, Osaka 565-0871, Japan

^bInnovative Catalysis Science Division, Institute for Open and Transdisciplinary Research Initiatives (ICS-OTRI), Osaka University, Suita, Osaka 565-0871, Japan

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Abstract

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Abstract

In this account, we describe our research on a Lewis acid-catalyzed insertion reaction of α-diazo esters into a carbon–carbon or carbon–halogen bond. Indium catalysts mediated not only the insertion of α-diazo esters into a carbon–carbon bond of alkyl acetates, alkyl ethers, acetals, and alkyl halides, but also a carbon–halogen bond of alkyl chlorides, bromides, and iodides. BF₃ specifically accelerated the insertion of α-diazo esters into a carbon–fluorine bond. The key to this catalysis is acetate, alkoxide, and halide shuttle systems mediated by a Lewis acid, in which the Lewis acid abstracts a leaving group from a starting substrate and releases the leaving group to the appropriate carbocation intermediate in the catalytic cycle.

1 Introduction

2 Acetate/Alkoxide Shuttle: Insertion Reaction of α-Diazo Esters into a Carbon–Carbon Bond of Alkyl Acetates, Alkyl Ethers, and Acetals

3 Halide Shuttle: Insertion Reaction of α-Diazo Esters into a Carbon–Carbon Bond of Alkyl Halides

4 Halide Shuttle: Insertion of α-Diazo Esters into a Carbon–Halogen Bond of Alkyl Halides

5 Conclusion

Key words

insertion reactions - C–C bonds - C–halogen bonds - diazo compounds - Lewis acids - alkyl acetates - alkyl ethers - acetals - alkyl halides

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References

References

Pioneering works:

1a Doering W. vonE, Hoffmann AK. J. Am. Chem. Soc. 1954; 76: 6162
1b DeMore WB, Pritchard HO, Davidson N. J. Am. Chem. Soc. 1959; 81: 5874
1c Doering W. vonE, Mole T. Tetrahedron 1960; 10: 65

2a Davies HM. L, Beckwith RE. J. Chem. Rev. 2003; 103: 2861
2b Jana S, Yujing G, Koenigs RM. Chem. Eur. J. 2021; 27: 1270
2c Dong S, Liu X, Feng X. Acc. Chem. Res. 2022; 55: 415

Selected reviews:

3a Souillart L, Cramer N. Chem. Rev. 2015; 115: 9410
3b Comprehensive Organometallic Chemistry, 3rd ed. Michael D, Mingos P, Crabtree RH. Elsevier Ltd; Amsterdam: 2007

Selected reviews:

4a Candeias NR, Paterna R, Gois PM. P. Chem. Rev. 2016; 116: 2937
4b Guttenberger N, Breinbauer R. Tetrahedron 2017; 73: 6815
4c Ciszewski ŁW, Rybicka-Jasińska K, Gryko D. Org. Biomol. Chem. 2019; 17: 432
4d Empel C, Koenigs RM. Synlett 2019; 30: 1929

5a Kanemasa S, Kanai T, Araki T, Wada E. Tetrahedron Lett. 1999; 40: 5055
5b Dudley ME, Morshed MM, Brennan CL, Islam MS, Ahmad MS, Atuu M, Branstetter B, Hossain MM. J. Org. Chem. 2004; 69: 7599
5c Dudley ME, Morshed MM, Hossain MM. Synthesis 2006; 1711
5d Hashimoto T, Naganawa Y, Maruoka K. J. Am. Chem. Soc. 2008; 130: 2434
5e Moebius DC, Kingsbury JS. J. Am. Chem. Soc. 2009; 131: 878
5f Fructos MR, Díaz-Requejo MM, Pérez PJ. Chem. Commun. 2009; 5153
5g Alves LG, Dazinger G, Veiros LF, Kirchner K. Eur. J. Inorg. Chem. 2010; 3160
5h Levesque P, Fournier P. J. Org. Chem. 2010; 75: 7033
5i Rendina VL, Moebius DC, Kingsbury JS. Org. Lett. 2011; 13: 2004
5j Gao L, Kang BC, Ryu DH. J. Am. Chem. Soc. 2013; 135: 14556
5k Gao L, Kang BC, Hwang GS, Ryu DH. Angew. Chem. Int. Ed. 2012; 51: 8322
5l Tan F, Pu M, He J, Li J, Yang J, Dong S, Liu X, Wu YD, Feng X. J. Am. Chem. Soc. 2021; 143: 2394
5m Bomio C, Kabeshov MA, Lit AR, Lau SH, Ehlert J, Battilocchio C, Ley SV. Chem. Sci. 2017; 8: 6071
5n Gini A, Bamberger J, Luis-Barrera J, Zurro M, Mas-Ballesté R, Alemán J, Mancheño OG. Adv. Synth. Catal. 2016; 358: 4049
5o Stockerl S, Danelzik T, Piekarski DG, Mancheño OG. Org. Lett. 2019; 21: 4535
5p Courant T, Pasco M, Lecourt T. Org. Lett. 2018; 20: 2757
5q Stopka T, Marzo L, Zurro M, Janich S, Würthwein EU, Daniliuc CG, Alemán J, Mancheño OG. Angew. Chem. Int. Ed. 2015; 54: 5049
5r Ba D, Wen S, Tian Q, Chen Y, Lv W, Cheng G. Nat. Commun. 2020; 11: 4219

6a Saito T, Yasuda M, Baba A. Synlett 2005; 1737
6b Saito T, Nishimoto Y, Yasuda M, Baba A. J. Org. Chem. 2006; 71: 8516
6c Saito T, Nishimoto Y, Yasuda M, Baba A. J. Org. Chem. 2007; 72: 8588
6d Nishimoto Y, Yasuda M, Baba A. Org. Lett. 2007; 9: 4931
6e Nishimoto Y, Saito T, Yasuda M, Baba A. Tetrahedron 2009; 65: 5462
6f Onishi Y, Nishimoto Y, Yasuda M, Baba A. Chem. Lett. 2011; 40: 1223
6g Onishi Y, Nishimoto Y, Yasuda M, Baba A. Org. Lett. 2011; 13: 2762
6h Onishi Y, Nishimoto Y, Yasuda M, Baba A. Org. Lett. 2014; 16: 1176
6i Nishimoto Y, Nishimura T, Yasuda M. Chem. Eur. J. 2015; 21: 8301
6j Nishimoto Y, Okita A, Baba A, Yasuda M. Molecules 2016; 1330
6k Nishimoto Y, Kita Y, Ueda H, Imaoka H, Chiba K, Yasuda M, Baba A. Chem. Eur. J. 2016; 22: 11837
6l Kita Y, Yata T, Nishimoto Y, Yasuda M. J. Org. Chem. 2018; 83: 740
6m Nakao S, Saikai M, Nishimoto Y, Yasuda M. Eur. J. Org. Chem. 2021; 77

Reviews for indium-catalyzed organic reactions:

7a Yadav JS, Antony A, George J, Reddy BV. S. Eur. J. Org. Chem. 2010; 591
7b Yang Y.-S, Wang S.-W, Long Y. Curr. Org. Chem. 2016; 20: 2865
7c Sestelo JP, Sarandeses LA, Martínez MM, Alonso-Marañón L. Org. Biomol. Chem. 2018; 16: 5733

8 Wang F, Yi J, Nishimoto Y, Yasuda M. Synthesis 2021; 53: 4004
9 Wang F, Nishimoto Y, Yasuda M. Angew. Chem. Int. Ed. 2022; 61: e202204462
10 Wang F, Nishimoto Y, Yasuda M. J. Am. Chem. Soc. 2021; 143: 20616
11 Wang F, Nishimoto Y, Yasuda M. Org. Lett. 2022; 24: 1706
12 Doyle MP, Trudell ML, Terpstra JW. J. Org. Chem. 1983; 48: 5146
13 Ring expansion of cyclic acetals with diazo esters catalyzed by Me₃SiOTf: Courant T, Pasco M, Lecourt T. Org. Lett. 2018; 20: 2757
14 Liu C, Sang S, Chen F, Yan Y, Zhang C, Huang W. J. Phys. Org. Chem. 2019; 32: e3902

15a Wang SH, Tu YQ, Tang M. Comprehensive Organic Synthesis, 2nd ed., Vol. 3. Knochel P. Elsevier; Amsterdam: 2014: 795
15b Gouygou M, Urrutigoïty M. Comprehensive Organic Synthesis, 2nd ed., Vol. 3. Knochel P. Elsevier; Amsterdam: 2014: 757

16 Modak A, Alegre-Requena JV, de Lescure L, Rynders KJ, Paton RS, Race NJ. J. Am. Chem. Soc. 2022; 144: 86

17a Masuda S, Nakajima T, Suga S. Bull. Chem. Soc. Jpn. 1983; 56: 1089
17b Li X, Li C, Zhang W, Lu X, Han S, Hong R. Org. Lett. 2010; 12: 1696
17c Tsuji Y, Richard JP. J. Phys. Org. Chem. 2016; 29: 557
17d Curtin DY, Crew MC. J. Am. Chem. Soc. 1954; 76: 3719
17e Cram DJ. J. Am. Chem. Soc. 1964; 86: 3767
17f Brown HC, Kim CJ. J. Am. Chem. Soc. 1968; 90: 2082

18a Stopka T, Marzo L, Zurro M, Janich S, Würthwein E.-U, Daniliuc CG, Alemán J, Mancheño OG. Angew. Chem. Int. Ed. 2015; 54: 5049
18b Zhang C, Jiang H, Zhu S. Chem. Commun. 2017; 53: 2677

Selected papers for bioactivities of dihydrodibenzo[b,f]oxepine derivatives and -dihydrodibenzo[b,f]thiepine derivatives:

19a Boegesoe KP, Liljefors T, Arnt J, Hyttel J, Pedersen H. J. Med. Chem. 1991; 34: 2023
19b Zhong M, Peng E, Huang N, Huang Q, Huq A, Lau M, Colonno R, Li L. Bioorg. Med. Chem. Lett. 2014; 24: 5738
19c Liu H, Liang H, Meng H, Deng X, Zhang X, Lai L. MedChemComm 2018; 9: 239
19d Platella C, Capasso D, Roccardi C, Musumeci D, DellaGreca M, Montesarchio D. Org. Biomol. Chem. 2021; 19: 9953
19e Zhao S, Zhang H, Jin H, Cai X, Zhang R, Jin Z, Yang W, Yu P, Zhang L, Liu Z. Eur. J. Med. Chem. 2021; 225: 113750
19f Cao S, Yang X, Zhang Z, Wu J, Chi B, Chen H, Yu J, Feng S, Xu Y, Li J, Zhang Y, Wang X, Wang Y. Eur. J. Med. Chem. 2022; 230: 114089

For selected reviews on C–F transformation, see:

20a Amii H, Uneyama K. Chem. Rev. 2009; 109: 2119
20b Shen Q, Huang YG, Liu C, Xiao JC, Chen QY, Guo Y. J. Fluorine Chem. 2015; 179: 14
20c Hamel JD, Paquin JF. Chem. Commun. 2018; 54: 10224
20d Fujita T, Fuchibe K, Ichikawa J. Angew. Chem. Int. Ed. 2019; 58: 390
20e Yan G, Qiu K, Guo M. Org. Chem. Front. 2021; 8: 3915

For the insertion reaction of a carbon unit into a C–F bond, see:

21a Sheppard WA, Webster OW. J. Am. Chem. Soc. 1973; 95: 2695
21b Glinka J, Fiscus D, Rao CB, Shechter H. Tetrahedron Lett. 1987; 28: 3221
21c Fujimoto H, Kodama T, Yamanaka M, Tobisu M. J. Am. Chem. Soc. 2020; 142: 17323
21d Yu X, Meng QY, Daniliuc CG, Studer A. J. Am. Chem. Soc. 2022; 144: 7072
21e Yoshida T, Ohta M, Emmei T, Kodama T, Tobisu M. Angew. Chem. Int. Ed. 2023; 62: e202303657

22a Olah GA, Kuhn S. J. Org. Chem. 1964; 29: 2317
22b Olah GA, Yamato T, Hashimoto T, Shih JG, Trivedi N, Singh BP, Piteau M, Olah JA. J. Am. Chem. Soc. 1987; 109: 3708
22c Hirano K, Fujita K, Yorimitsu H, Shinokubo H, Oshima K. Tetrahedron Lett. 2004; 45: 2555
22d Hirano K, Yorimitsu H, Oshima K. Org. Lett. 2004; 6: 4873

23a Caputo CB, Stephan DW. Organometallics 2012; 31: 27
23b Dryzhakov M, Moran J. ACS Catal. 2016; 6: 3670

24a Henne AL, Newman MS. J. Am. Chem. Soc. 1938; 60: 1697
24b Burton DJ, Briney GG. J. Org. Chem. 1970; 35: 3036
24c Villani FJ, Mann TA, Wefer EA, Hannon J, Larca LL, Landon MJ, Spivak W, Vashi D, Tozzi S, Danko G, del Prado M, Lutz MJ. J. Med. Chem. 1975; 18: 1
24d Riera J, Castañer J, Carilla J, Robert A. Tetrahedron Lett. 1989; 30: 3825
24e Castañer J, Riera J, Carilla J, Robert A, Molins E, Miravitlles C. J. Org. Chem. 1991; 56: 103
24f Carilla J, Fajari L, Garcia R, Julia L, Marcos C, Riera J, Whitaker CR, Rius J, Aleman C. J. Org. Chem. 1995; 60: 2721
24g Ramchandani RK, Wakharkar RD, Sudalai A. Tetrahedron Lett. 1996; 37: 4063

25 Ooi T, Uraguchi D, Kagoshima N, Maruoka K. Tetrahedron Lett. 1997; 38: 5679

For selected papers on fluoride abstraction by aluminum Lewis acids, see:

26a Fuchibe K, Hatta H, Oh K, Oki R, Ichikawa J. Angew. Chem. Int. Ed. 2017; 56: 5890
26b Meißner G, Kretschmar K, Braun T, Kemnitz E. Angew. Chem. Int. Ed. 2017; 56: 16338
26c Fuchibe K, Oki R, Hatta H, Ichikawa J. Chem. Eur. J. 2018; 24: 17932
26d Fuchibe K, Fushihara T, Ichikawa J. Org. Lett. 2020; 22: 2201

For selected recent papers, see:

27a Wu J, Li X, Qi X, Duan X, Cracraft WL, Guzei IA, Liu P, Tang W. J. Am. Chem. Soc. 2019; 141: 19902
27b Devi L, Shukla R, Rastogi N. Org. Biomol. Chem. 2019; 17: 135
27c Song L, Ni D, Jia S, Pi R, Dong S, Yang F, Tang J, Liu S. Org. Lett. 2020; 22: 1846

For selected recent papers, see:

28a Davies PW, Albrecht SJ. C, Assanelli G. Org. Biomol. Chem. 2009; 7: 1276
28b Liu Z, Sivaguru P, Zanoni G, Anderson EA, Bi X. Angew. Chem. Int. Ed. 2018; 57: 8927
28c Luo K, Mao S, He K, Yu X, Pan J, Lin J, Shao Z, Jin Y. ACS Catal. 2020; 10: 3733

Selected recent papers:

29a Tayama E, Yanaki T, Iwamoto H, Hasegawa E. Eur. J. Org. Chem. 2010; 6719
29b Hong X, Lu L, Shen Q. Synlett 2019; 30: 1602
29c Li M, Sun Y, Xie Y, Yu Y, Huang F, Huang H. Chem. Commun. 2020; 56: 11050

30 Yan XW, Zhang Q, Wei W, Ji JX. Tetrahedron Lett. 2014; 55: 3750
31 Erdmann P, Leitner J, Schwarz J, Greb L. ChemPhysChem 2020; 21: 987
32 Lingam VS. P. R, Thomas A, Dahale DH, Rathi VE, Khairatkar-Joshi N, Mukhopadhyay I. Guanidine Derivatives as TRPC Modulators, International Patent WO 2014016766 A1, January 30, 2014