Substrate-Controlled Regioselective Iodooxygenation of Olefins

Xiaoqing Li; Kun Chen; Yucai Tang; Huanhuan Zhu; Feng Chen; Xinhuan Yan; Xiangsheng Xu

doi:10.1055/s-0037-1609968

Synlett, Table of Contents

Synlett 2018; 29(12): 1634-1638
DOI: 10.1055/s-0037-1609968

letter

Substrate-Controlled Regioselective Iodooxygenation of Olefins

Authors

Xiaoqing Li*

^aCollege of Chemical Engineering, Zhejiang University of Technology, Hangzhou 310014, P. R. of China Email: xqli@zjut.edu.cn Email: future@zjut.edu.cn
Kun Chen

^aCollege of Chemical Engineering, Zhejiang University of Technology, Hangzhou 310014, P. R. of China Email: xqli@zjut.edu.cn Email: future@zjut.edu.cn
Yucai Tang

^bCollege of Chemistry and Material Engineering, Hunan University of Arts and Science, Changde, 415000, P. R. of China
Huanhuan Zhu

^aCollege of Chemical Engineering, Zhejiang University of Technology, Hangzhou 310014, P. R. of China Email: xqli@zjut.edu.cn Email: future@zjut.edu.cn
Feng Chen

^aCollege of Chemical Engineering, Zhejiang University of Technology, Hangzhou 310014, P. R. of China Email: xqli@zjut.edu.cn Email: future@zjut.edu.cn
Xinhuan Yan

^aCollege of Chemical Engineering, Zhejiang University of Technology, Hangzhou 310014, P. R. of China Email: xqli@zjut.edu.cn Email: future@zjut.edu.cn
Xiangsheng Xu*

^aCollege of Chemical Engineering, Zhejiang University of Technology, Hangzhou 310014, P. R. of China Email: xqli@zjut.edu.cn Email: future@zjut.edu.cn

Abstract

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Abstract

An unexpected regioselective I₂/TBHP-mediated 1,2-iodooxygenation of alkenes with N-hydroxylamines is described. The reaction proceeds through a radical coupling mechanism or a iodonium mechanism, which is controlled by the structures of both N-hydroxylamines and alkenes, to form vicinal iodo-substituted N-alkoxyamines regioselectively. Both the iodo and alkoxyamine group of the resulting products offer rich possibilities of synthetic manipulations.

Key words

iodooxygenation - regioselectivity - alkenes - N-hydroxyphthalimide - 1-hydroxybenzotriazole

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References

References and Notes

1a Jensen KH. Webb JD. Sigman MS. J. Am. Chem. Soc. 2010; 132: 17471
1b Egami H. Sodeoka M. Angew. Chem. Int. Ed. 2014; 53: 8294
1c Ouyang X.-H. Song R.-J. Hu M. Yang Y. Li J.-H. Angew. Chem. Int. Ed. 2016; 55: 3187
1d Liu Y. Xie Y. Wang H. Huang H. J. Am. Chem. Soc. 2016; 138: 4314
1e Banik SM. Medley JW. Jacobsen EN. J. Am. Chem. Soc. 2016; 138: 5000
1f Ji X. Huang H. Wu W. Jiang H. J. Am. Chem. Soc. 2013; 135: 5286
1g Li Z. Zhang C. Zhu L. Liu C. Li C. Org. Chem. Front. 2014; 1: 100
1h Yu X.-L. Chen J.-R. Chen D.-Z. Xiao W.-J. Chem. Commun. 2016; 52: 8275
1i Lin J.-S. Dong X.-Y. Li T.-T. Jiang N.-C. Tan B. Liu X.-YJ. J. Am. Chem. Soc. 2016; 138: 9357
1j Carboni A. Dagousset G. Magnier E. Masson G. Chem. Commun. 2014; 50: 14197
1k Courant T. Masson G. J. Org. Chem. 2016; 81: 6945

2a Giglio BC. Schmidt VA. Alexanian EJ. J. Am. Chem. Soc. 2011; 133: 13320
2b Bataille CJ. R. Donohoe T. J. Chem. Soc. Rev. 2011; 40: 114
2c Lu Q. Liu Z. Luo Y. Zhang G. Huang Z. Wang H. Liu C. Miller JT. Lei A. Org. Lett. 2015; 17: 3402
2d Tan B. Toda N. Barbas III CF. Angew. Chem. Int. Ed. 2012; 51: 12538
2e Lu Q. Liu C. Huang Z. Ma Y. Zhang J. Lei A. Chem. Commun. 2014; 50: 14101
2f Xue Q. Xie J. Xu P. Hu K. Cheng Y. Zhu C. ACS Catal. 2013; 3: 1365
2g Schmidt VA. Alexanian EJ. Angew. Chem. Int. Ed. 2010; 49: 4491
2h Ghosh R. Olofsson B. Org. Lett. 2014; 16: 1830
2i Reddi RN. Prasad PK. Sudalai A. Org. Lett. 2014; 16: 5674

3a Dian L. Wang S. Du Y. Adv. Synth. Catal. 2015; 357: 3836
3b Mazzonna M. Bietti M. DiLabio GA. Lanzalunga O. Salamone M. J. Org. Chem. 2014; 79: 5209
3c Huang L. Zheng S.-C. Tan B. Liu X.-Y. Org. Lett. 2015; 17: 1589
3d Baciocchi E. Bietti M. Lanzalunga O. Lapi A. Raponi D. J. Org. Chem. 2010; 75: 1378
3e Recupero FC. Punta C. Chem. Rev. 2007; 107: 3800
3f Patil AS. Mo D.-L. Wang H.-Y. Mueller DS. Anderson LL. Angew. Chem. Int. Ed. 2012; 51: 7799

4a Bag R. De P B. Pradhan S. Punniyamurthy T. Eur. J. Org. Chem. 2017; 5424
4b Samanta S. Donthiri RR. Ravi C. Adimurthy S. J. Org. Chem. 2016; 81: 3457
4c Andia AA. Miner MR. Woerpel KA. Org. Lett. 2015; 17: 2704
4d Bag R. Sar D. Punniyamurthy T. Org. Biomol. Chem. 2016; 14: 3246
4e Zhang J.-Z. Tang Y. Adv. Synth. Catal. 2016; 358: 752
4f Lv Y. Wang X. Cui H. Sun K. Pu W. Li G. Wu Y. He J. Ren X. RSC Adv. 2016; 6: 74917

5 Xia X.-F. Zhu S.-L. Gu Z. Wang H. Li W. Liu X. Liang Y.-M. J. Org. Chem. 2015; 80: 5572
6 Zhang T.-S. Xiong Y.-J. Hao W. Zhu X.-T. Wang S.-L. Li G. Tu S.-J. Jiang B. J. Org. Chem. 2016; 81: 9350

7a Ando T. Kano D. Minakata S. Ryu I. Komatsu M. Tetrahedron 1998; 54: 13485
7b Li Y.-X. Wang H.-X. Ali S. Xia X.-F. Liang Y.-M. Chem. Commun. 2012; 48: 2343
7c Donohoe TJ. Kabeshov MA. Rathi AH. Smith IE. D. Org. Biomol. Chem. 2012; 10: 1093
7d Donohoe TJ. Kabeshov MA. Rathi AH. Smith IE. Org. Biomol. Chem. 2012; 10: 1093
7e Kariya A. Yamaguchi T. Nobuta T. Tada N. Itoh A. RSC Adv. 2014; 4: 13191
7f Sun K. Ma F. Zhang Z. Zhang G. RSC. Adv. 2015; 5: 82492
7g Finkbeiner P. Nachtsheim BJ. Synthesis 2013; 45: 979

8a Tang S. Wu Y. Liao W. Bai R. Liu C. Lei A. Chem. Commun. 2014; 50: 4496
8b Xiao F. Chen H. Xie H. Chen S. Yang L. Deng G.-J. Org. Lett. 2014; 16: 50
8c Liu C. Zhu M. Wei W. Yang D. Wang H. Org. Chem. Front. 2015; 2: 1356
8d Li X. Xu X. Shi X. Tetrahedron Lett. 2013; 54: 3071
8e Fan Y. Zhou B. Chen K. Wang B. Li X. Xu X. Synlett 2017; 28: 1659

9 General Procedure for the Synthesis of Compounds 2Alkenes (0.3 mmol) and TBHP (0.6 mmol) was added to a solution of 1-hydroxybenzotriazole (0.36 mmol) and iodide (0.15 mmol) in 2 mL of DCE. After the reaction mixture was stirred at 40 °C for 2 h, the solvent was removed under reduced pressure, and the residual was treated with silica gel chromatography to give compounds 2.1-(2-Iodo-2-phenylethoxy)-1H-benzo[d][1,2,3]triazole (2a)Colorless oil. ¹H NMR(500 MHz, CDCl₃): δ = 7.93 (d, J = 8.3 Hz, 1 H), 7.39–7.32 (m, 6 H), 7.29 (m, 2 H), 5.69 (t, J = 7.0Hz, 1 H), 3.93 (dd, J = 10.8, 7.1 Hz, 1 H), 3.71 (dd, J = 10.8, 7.0 Hz, 1 H). ¹³C NMR (125 MHz, CDCl₃): δ = 143.12, 135.4, 130.1, 128.8, 127.90,127.87, 127.5, 124.4, 120.0, 108.8, 91.8, 2.9. HRMS (ESI): m/z calcd for C₁₄H₁₃IN₃O [M + H⁺]: 366.0098; found: 366.0096.
10 General Procedure for the Synthesis of Compounds 3Alkenes (1.5 mmol) and TBHP (0.6 mmol) was added to a solution of N-hydroxyphthalimide (0.3 mmol) and iodide (0.15 mmol) in 2 mL of DCE. After the reaction mixture was stirred at 80 °C for 6 h, the solvent was removed under reduced pressure, and the residual was treated with silica gel chromatography to give compounds 3.2-(2-Iodo-2-phenylethoxy)isoindoline-1,3-dione (3a)White solid; mp 134–135 °C. ¹H NMR (500 MHz, CDCl₃): δ = 7.77 (m, 2 H), 7.73 (m, 2 H), 7.52 (dd, J = 5.2, 3.4 Hz, 2 H), 7.31–7.27 (m, 2 H), 7.22–7.18 (m, 1 H), 5.51 (dd, J = 9.8, 5.7 Hz, 1 H), 4.94–4.89 (m, 1 H), 4.69 (dd, J = 10.8, 5.7 Hz, 1 H). ¹³C NMR (125 MHz, CDCl₃): δ = 163.1, 139.7, 134.6, 128.8, 128.6, 128.5, 127.8, 123.5, 81.3, 25.1. HRMS (ESI): m/z calcd for C₁₆H₁₃INO₃ [M + H⁺]: 393.9935; found: 393.9928.

11a Kumar M. Scobie M. Mashuta MS. Hammond GB. Xu B. Org. Lett. 2013; 44: 724

12a Bedrac L. Iskra J. Tetrahedron Lett. 2012; 53: 5555
12b Bortolini O. Bottai M. Chiappe C. Contec V. Pieraccinib D. Green Chem. 2002; 4: 621
12c Kajigaeshi S. Masayuki M. Fujisaki S. Kakinami T. Okamto T. Bull. Chem. Soc. Jpn. 1990; 63: 3033

Supplementary Material

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