Homologation of Alkyl Acetates, Alkyl Ethers, Acetals, and Ketals by Formal Insertion of Diazo Compounds into a Carbon–Carbon Bond

Fei Wang; Junyi Yi; Yoshihiro Nishimoto; Makoto Yasuda

doi:10.1055/a-1523-1551

Synthesis, Table of Contents

Synthesis 2021; 53(21): 4004-4019
DOI: 10.1055/a-1523-1551

feature

Homologation of Alkyl Acetates, Alkyl Ethers, Acetals, and Ketals by Formal Insertion of Diazo Compounds into a Carbon–Carbon Bond

Fei Wang

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

,

Junyi Yi

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

,

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

› Author Affiliations

Abstract

All articles of this category

Abstract

Homologation of alkyl acetates, alkyl ethers, acetals, and ketals was accomplished via formal insertion of diazo esters into carbon–carbon σ-bonds. The combined Lewis acid InI₃ with Me₃SiBr catalyzed the homologation of alkyl acetates and alkyl ethers. That of acetals and ketals was catalyzed solely by the use of InBr₃. The key point of the homologation mechanism is that the indium-based Lewis acids have the appropriate amount of Lewis acidity to achieve both the abstraction and release of leaving groups. The abstraction of a leaving group by an indium-based Lewis acid and the electrophilic addition of carbocation or oxonium intermediates to diazo esters followed by the rearrangement of carbon substituents provide the corresponding cation intermediates. Finally, the leaving group that is captured by the Lewis acid bonds with cation intermediates to furnish the homologated products.

Key words

alkyl acetates - alkyl ethers - acetals - ketals - carbocations - diazo compound - homologation - indium

Full Text

References

References

Homologation via one-carbon-insertion into C–C σ-bonds:

1a Xia Y, Liu Z, Ge R, Ye F, Hossain M, Zhang Y, Wang J. J. Am. Chem. Soc. 2014; 136: 3013
1b Yada A, Fujita S, Murakami M. J. Am. Chem. Soc. 2014; 136: 7217
1c Liu Z, Sivaguru P, Zanoni G, Anderson EA, Bi X. Angew. Chem. Int. Ed. 2018; 57: 8927
1d Liu Z, Zhang X, Virelli M, Zanoni G, Anderson EA, Bi X. iScience 2018; 8: 54

A review:

1e Candeias NR, Paterna R, Gois PM. P. Chem. Rev. 2016; 116: 2937

Reviews for homologation via one-carbon-insertion into X–H (X = C, O, S, N, etc.) bonds:

2a Davies HM. L, Beckwith RE. J. Chem. Rev. 2003; 103: 2861
2b Katritzky AR, Bobrov S. ARKIVOC 2005; (x): 174
2c Thomas SP, French RM, Jheengut V, Aggarwal VK. Chem. Rec. 2009; 9: 24
2d Doyle MP, Duffy R, Ratnikov M, Zhou L. Chem. Rev. 2010; 110: 704
2e Zhu S.-F, Zhou Q.-L. Acc. Chem. Res. 2012; 45: 1365
2f Gillingham D, Fei N. Chem. Soc. Rev. 2013; 42: 4918
2g Egger J, Carreira EM. Nat. Prod. Rep. 2014; 31: 449
2h Lombard FJ, Coster MJ. Org. Biomol. Chem. 2015; 13: 6419
2i Castoldi L, Monticelli S, Senatore R, Ielo L, Pace V. Chem. Commun. 2018; 54: 6692

3 Homologation via one-carbon-insertion into a C–B bond: Bomio C, Kabeshov MA, Lit AR, Lau SH, Ehlert J, Battilocchio C, Ley SV. Chem. Sci. 2017; 8: 6071

Reviews for use of diazo compounds as a one-carbon-source:

4a Ye T, McKervey MA. Chem. Rev. 1994; 94: 1091
4b Doyle MP, McKervey MA, Ye T. Modern Catalytic Methods for Organic Synthesis with Diazo Compounds . Wiley-Interscience; New York: 1998
4c Zhang Z, Wang J. Tetrahedron 2008; 64: 6577
4d Davies HM. L, Manning JR. Nature 2008; 451: 417
4e Barluenga J, Valdés C. Angew. Chem. Int. Ed. 2011; 50: 7486
4f Shao Z, Zhang H. Chem. Soc. Rev. 2012; 41: 560
4g Xiao Q, Zhang Y, Wang J. Acc. Chem. Res. 2013; 46: 236
4h Liu Z, Wang J. J. Org. Chem. 2013; 78: 10024
4i Xia Y, Zhang Y, Wang J. ACS Catal. 2013; 3: 2586
4j Guttenberger N, Breinbauer R. Tetrahedron 2017; 73: 6815

5a Kanemasa S, Kanai T, Araki T, Wada E. Tetrahedren 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 Fructos MR, Díaz-Requejo MM, Pérez PJ. Chem. Commun. 2009; 5153
5f Alves LG, Dazinger G, Veiros LF, Kirchner K. Eur. J. Inorg. Chem. 2010; 3160
5g Levesque P, Fournier P. J. Org. Chem. 2010; 75: 7033
5h Gao L, Kang BC, Ryu DH. J. Am. Chem. Soc. 2013; 135: 14556
5i 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

6 Cheng reported rhodium-catalyzed formal insertion of O–C(sp³)–C(sp²) into C–C σ-bonds of 1,3-dicarbonyl compounds using diazo esters and DMF: Ba D, Wen S, Tian Q, Chen Y, Lv W, Cheng G. Nat. Commun. 2020; 11: 4219
7 Doyle MP, Trudell ML, Terpstra JW. J. Org. Chem. 1983; 48: 5146
8 Ring expansion of cyclic acetals with diazo esters catalyzed by Me₃SiOTf: Courant T, Pasco M, Lecourt T. Org. Lett. 2018; 20: 2757

9a Gini A, Bamberger J, Luis-Barrera J, Zurro M, Mas-Ballesté R, Alemán J, Mancheño OG. Adv. Synth. Catal. 2016; 358: 4049
9b Stockerl S, Danelzik T, Piekarski DG, Mancheño OG. Org. Lett. 2019; 21: 4535

10 Stopka T, Marzo L, Zurro M, Janich S, Würthwein EU, Daniliuc CG, Alemán J, Mancheño OG. Angew. Chem. Int. Ed. 2015; 54: 5049

11a Saito T, Yasuda M, Baba A. Synlett 2005; 1737
11b Saito T, Nishimoto Y, Yasuda M, Baba A. J. Org. Chem. 2006; 71: 8516
11c Saito T, Nishimoto Y, Yasuda M, Baba A. J. Org. Chem. 2007; 72: 8588
11d Onishi Y, Nishimoto Y, Yasuda M, Baba A. Chem. Lett. 2011; 40: 1223
11e Onishi Y, Nishimoto Y, Yasuda M, Baba A. Org. Lett. 2011; 13: 2762

12 CCDC 2075523 (3aa) contains the supplementary crystallographic data for this paper. The data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/structures
13 Liu C, Sang S, Chen F, Yan Y, Zhang C, Huang W. J. Phys. Org. Chem. 2019; 32: e3902

14a Onishi Y, Nishimoto Y, Yasuda M, Baba A. Org. Lett. 2014; 16: 1176
14b Nishimoto Y, Nishimura T, Yasuda M. Chem. Eur. J. 2015; 21: 8301
14c Nishimoto Y, Okita A, Baba A, Yasuda M. Molecules 2016; 21: 1330
14d Nishimoto Y, Kita Y, Ueda H, Imaoka H, Chiba K, Yasuda M, Baba A. Chem. Eur. J. 2016; 22: 11837
14e Kita Y, Yata T, Nishimoto Y, Yasuda M. J. Org. Chem. 2018; 83: 740
14f Nakao S, Saikai M, Nishimoto Y, Yasuda M. Eur. J. Org. Chem. 2021; 77

Indium-catalyzed transformation of acetals:

15a Ranu BC, Das A, Samanta S. Synlett 2002; 727
15b Gregg BT, Golden KC, Quinn JF. J. Org. Chem. 2007; 72: 5890

Reviews for indium-catalyzed organic reactions:

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

17a Wang SH, Tu YQ, Tang M. In Comprehensive Organic Synthesis, 2nd ed., Vol. 3. Knochel P. Elsevier; Amsterdam: 2014: 795
17b Gouygou M, Urrutigoïty M. In Comprehensive Organic Synthesis, 2nd ed., Vol. 3. Knochel P. Elsevier; Amsterdam: 2014: 757

18 Mamidi N, Manna D. J. Org. Chem. 2013; 78: 2386
19 Laurent M, Marchand-Brynaert J. Synthesis 2000; 667
20 Sakai N, Moriya T, Konakahara T. J. Org. Chem. 2007; 72: 5920
21 Estopiñá-Durán S, Donnelly LJ, Mclean EB, Hockin BM, Slawin AM. Z, Taylor JE. Chem. Eur. J. 2019; 25: 3950
22 Redwan IN, Grøtli M. J. Org. Chem. 2012; 77: 7071
23 Nag E, Gorantla SM. N. V. T, Arumugam S, Kulkarni A, Mondal KC, Roy S. Org. Lett. 2020; 22: 6313
24 Hodgson DM, Angrish D. Chem. Eur. J. 2007; 13: 3470
25 Davis OA, Croft RA, Bull JA. Chem. Commun. 2015; 51: 15446
26 Luo X, Chen G, He L, Huang X. J. Org. Chem. 2016; 81: 2943
27 Ye F, Wang C, Zhang Y, Wang J. Angew. Chem. Int. Ed. 2014; 53: 11625
28 Luo X, Chen G, He L, Huang X. J. Org. Chem. 2016; 81: 2943
29 Costin TA, Dutra LG, Bortoluzzi AJ, Sá MM. Tetrahedron 2017; 73: 4549
30 Meng L, Wu P, Fang J, Xiao Y, Xiao X, Tu G, Ma X, Teng S, Zeng J, Wan Q. J. Am. Chem. Soc. 2019; 141: 11775
31 Korneev S, Richter C. Synthesis 1995; 1248
32 Baxter M, Bolshan Y. Chem. Eur. J. 2015; 21: 13535
33 Zhang M, Wang Y, Yang Y, Hua X. Adv. Synth. Catal. 2012; 354: 981
34 Xavier T, Rayapin C, Gall EL, Presset M. Chem. Eur. J. 2019; 25: 13824
35 Kawajiri T, Kato M, Nakata H, Goto R, Aibara S, Ohta R, Fujioka H, Sajiki H, Sawama Y. J. Org. Chem. 2019; 84: 3853
36 Blümel M, Nagasawa S, Blackford K, Hare SR, Tantillo DJ, Sarpong R. J. Am. Chem. Soc. 2018; 140: 9291
37 Bonazzi S, Cheng B, Wzorek JS, Evans DA. J. Am. Chem. Soc. 2013; 135: 9338
38 Lan J, Jiang G, Yang J, Zhu H, Le Z, Xie Z. Synthesis 2020; 52: 2121
39 Liu C, Shen Y, Xiao Z, Yang H, Han X, Yuan K, Ding Y. Green Chem. 2019; 21: 4030
40 Yue H, Guo L, Lee SC, Liu X, Rueping M. Angew. Chem. Int. Ed. 2017; 56: 3972
41 Rossolini T, Ferko B, Dixon DJ. Org. Lett. 2019; 21: 6668
42 Baekstroem P, Stridh K, Li L, Norin T. Acta Chem. Scand., Ser. B. 1987; 41: 442
43 Wu Z, Leboeuf D, Retailleau P, Gandon V, Marinetti A, Voituriez A. Chem. Commun. 2017; 53: 7026
44 Konishi A, Okada Y, Nakano M, Sugisaki K, Sato K, Takui T, Yasuda M. J. Am. Chem. Soc. 2017; 139: 15284
45 Tanemura K, Suzuki T. Chem. Lett. 2015; 44: 797

Supplementary Material

Supporting Information