Oxidative β-Halogenation of Alcohols: A Concise and Diastereoselective Approach to Halohydrins

Lingsheng Ai; Weijin Wang; Jialiang Wei; Qing Li; Song Song; Ning Jiao

doi:10.1055/s-0037-1610385

Synlett, Inhaltsverzeichnis

CC BY ND NC 4.0 · Synlett 2019; 30(04): 437-441
DOI: 10.1055/s-0037-1610385

letter

Copyright with the author

Oxidative β-Halogenation of Alcohols: A Concise and Diastereoselective Approach to Halohydrins

Lingsheng Ai

^aState Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University, Xue Yuan Rd. 38, Beijing 100191, P. R. of China eMail: ssong@bjmu.edu.cn eMail: jiaoning@pku.edu.cn

,

Weijin Wang

^aState Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University, Xue Yuan Rd. 38, Beijing 100191, P. R. of China eMail: ssong@bjmu.edu.cn eMail: jiaoning@pku.edu.cn

,

Jialiang Wei

^aState Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University, Xue Yuan Rd. 38, Beijing 100191, P. R. of China eMail: ssong@bjmu.edu.cn eMail: jiaoning@pku.edu.cn

,

Qing Li

^aState Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University, Xue Yuan Rd. 38, Beijing 100191, P. R. of China eMail: ssong@bjmu.edu.cn eMail: jiaoning@pku.edu.cn

,

Song Song*

^aState Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University, Xue Yuan Rd. 38, Beijing 100191, P. R. of China eMail: ssong@bjmu.edu.cn eMail: jiaoning@pku.edu.cn

^bState Key Laboratory of Drug Research Shanghai Institute of Materia Medical Chinese Academy of Sciences, Shanghai 201203, P. R. of China

,

Ning Jiao *

^aState Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University, Xue Yuan Rd. 38, Beijing 100191, P. R. of China eMail: ssong@bjmu.edu.cn eMail: jiaoning@pku.edu.cn

^bState Key Laboratory of Drug Research Shanghai Institute of Materia Medical Chinese Academy of Sciences, Shanghai 201203, P. R. of China

› Institutsangaben

Abstract

Alle Artikel dieser Rubrik

Published as part of the 30 Years SYNLETT – Pearl Anniversary Issue

Abstract

β-Halohydrins bearing transformable halo- and hydroxyl groups, are easily converted into various valuable blocks in organic and pharmaceutical synthesis. A diastereoselective β-halogenation of benzylic alcohols was achieved under simple and low-cost conditions, which provided a direct synthesis of β-halohydrins. The simple reaction conditions, easily available reagents, high diastereoselectivities, and additional oxidant-free make this reaction very attractive and practical.

Key words

halogenation - alcohols - dimethyl sulfoxide - halohydrins - oxidation

Volltext

Referenzen

References
1 Gribble GW. J. Chem. Educ. 2004; 81: 1441
2 Dagani MJ, Barda HJ, Benya TJ, Sanders DC. Bromine Compounds in Ullmann’s Encyclopedia of Industrial Chemistry . Wiley-VCH; Weinheim: 2002
3 Organic Bromine and Iodine Compounds in The Handbook of Environmental Chemistry. Neilson AH. Springer; Berlin, Heidelberg: 2003
4 Buckles RE, Maurer JE. J. Org. Chem. 1953; 18: 1585
5 Naimi-Jamal MR, Mokhtari J, Dekamin MG, Kaupp G. Eur. J. Org. Chem. 2009; 3567

6a Ren WM, Liu Y, Lu XB. J. Org. Chem. 2014; 79: 9771
6b Naeimi H. J. Chin. Chem. Soc. 2008; 55: 1156

7 Bhosale SS, Joshi PL, Rao AS. Org. Prep. Proced. Int. 1992; 24: 695

For selected reviews on enzyme-catalyzed oxidative halogenations, see:

8a Vaillancourt FH, Yeh E, Vosburg DA, Garneau-Tsodikova S, Walsh CT. Chem. Rev. 2006; 106: 3364
8b Lewis JC, Coelho PS, Arnold FH. Chem. Soc. Rev. 2011; 40: 2003

9a Podgoršek A, Zupan M, Iskra J. Angew. Chem. Int. Ed. 2009; 48: 8424
9b Yonehara K, Kamata K, Yamaguchi K, Mizuno N. Chem. Commun. 2011; 47: 1692
9c Yang L, Lu Z, Stahl SS. Chem. Commun. 2009; 45: 6460
9d Podgorsek A, Eissen M, Fleckenstein J, Stavber S, Zupan M, Iskra J. Green Chem. 2009; 11: 120
9e Zhang GF, Liu RH, Xu Q, Ma LX, Liang XM. Adv. Synth. Catal. 2006; 348: 862
9f Yu T.-Y, Wang Y, Hu X.-Q, Xu P.-F. Chem. Commun. 2014; 50: 7817
9g Wang G.-W, Gao J. Green Chem. 2012; 14: 1125
9h Adimurthy S, Ghosh S, Patoliya PU, Ramachandraiah G, Agrawal M, Gandhi MR, Upadhyay SC, Ghosh PK, Ranu BC. Green Chem. 2008; 10: 232
9i Rana S, Bag S, Patra T, Maiti D. Adv. Synth. Catal. 2014; 356: 2453
9j Bedrač L, Iskra J. Adv. Synth. Catal. 2013; 355: 1243

10a Sels BF, De Vos DE, Jacobs PA. J. Am. Chem. Soc. 2001; 123: 8350
10b Pandit P, Gayen KS, Khamarui S, Chatterjee N, Maiti DK. Chem. Commun. 2011; 47: 6933
10c Dewkar GK, Narina SV, Sudalai A. Org. Lett. 2003; 5: 4501
10d Yang X, Wu J, Mao X, Jamison TF, Hatton TA. Chem. Commun. 2014; 50: 3245
10e Darensbourg DJ, Wilson SJ. J. Am. Chem. Soc. 2011; 133: 18610
10f Kozhushkov SI, Yufit DS, de Meijere A. Adv. Synth. Catal. 2005; 347: 255
10g Sels B, De Vos D, Buntinx M, Pierard F, Kirsch-De Mesmaeker A, Jacobs P. Nature 1999; 400: 855
10h Barluenga J, Gonzalez JM, Campos PJ, Asensio G. Angew. Chem. 1985; 97: 341
10i Rao DS, Reddy TR, Babachary K, Kashyap S. Org. Biomol. Chem. 2016; 14: 7529
10j Ashikari Y, Shimizu A, Nokami T, Yoshida J. J. Am. Chem. Soc. 2013; 135: 16070

For α-functionalization of alcohols, see:

11a Jeffrey JL, Terrett JA, MacMillan DW. Science 2015; 349: 1532
11b Shi L, Tu Y.-Q, Wang M, Zhang F.-M, Fan C.-A, Zhao Y.-M, Xia W.-J. J. Am. Chem. Soc. 2005; 127: 10836
11c Zhang S.-Y, Tu Y.-Q, Fan C.-A, Zhang F.-M, Shi L. Angew. Chem. Int. Ed. 2009; 48: 8761

For β-functionalization of alcohols, see:

11d Espino CG, Du Bois J. Angew. Chem. Int. Ed. 2001; 40: 598
11e Ren Z, Mo F, Dong G. J. Am. Chem. Soc. 2012; 134: 16991
11f Wappes EA, Nakafuku KM, Nagib DA. J. Am. Chem. Soc. 2017; 139: 10204
11g Bunescu A, Butcher TW, Hartwig JF. J. Am. Chem. Soc. 2018; 140: 1502

For γ-functionalization of alcohols, see:

11h Simmons EM, Hartwig JF. Nature 2012; 483: 70
11i Alderson JM, Phelps AM, Scamp RJ, Dolan NS, Schomaker JM. J. Am. Chem. Soc. 2014; 136: 16720
11j Espino CG, Wehn PM, Chow J, Du Bois J. J. Am. Chem. Soc. 2001; 123: 6935
11k Chen K, Richter JM, Baran PS. J. Am. Chem. Soc. 2008; 130: 7247
11l Zalatan DN, Du Bois J. J. Am. Chem. Soc. 2008; 130: 9220

For δ-functionalization of alcohols, see:

11m Hu A, Guo J.-J, Pan H, Tang H, Gao Z, Zuo Z. J. Am. Chem. Soc. 2018; 140: 1612
11n Wu X, Wang M, Huan L, Wang D, Wang J, Zhu C. Angew. Chem. Int. Ed. 2018; 57: 1640
11o Zhang J, Li Y, Zhang F, Hu C, Chen Y. Angew. Chem. Int. Ed. 2016; 55: 1872
11p Wang CY, Harms K, Meggers E. Angew. Chem. Int. Ed. 2016; 55: 13495

12a Cami-Kobeci G, Williams JM. J. Synlett 2003; 124
12b Ajvazi N, Stavber S. Molecules 2016; 21: 1325
12c Klimczyk S, Huang X, Farès C, Maulide N. Org. Biomol. Chem. 2012; 10: 4327

13a Song S, Sun X, Li X, Yuan Y, Jiao N. Org. Lett. 2015; 17: 2886
13b Liang Y.-F, Li X, Wang X, Zou M, Tang C, Liang Y, Song S, Jiao N. J. Am. Chem. Soc. 2016; 138: 12271
13c Liang Y.-F, Wu K, Song S, Li X, Huang X, Jiao N. Org. Lett. 2015; 17: 876
13d Song S, Li X, Sun X, Yuan Y, Jiao N. Green Chem. 2015; 17: 3285
13e Song S, Zhang Y, Yeerlan A, Zhu B, Liu J, Jiao N. Angew. Chem. Int. Ed. 2017; 56: 2487

For reviews on DMSO as the reagent in organic synthesis, see:

14a Wu X.-F, Natte K. Adv. Synth. Catal. 2016; 358: 336
14b Jones-Mensah E, Karki M, Magolan J. Synthesis 2016; 48: 1421

15a Huang H, Tang L, Liu Q, Xi Y, He G, Zhu H. Chem. Commun. 2016; 52: 5605
15b Kawaguchi T, Miyata H, Ataka K, Mae K, Yoshida J. Angew. Chem. Int. Ed. 2005; 44: 2413
15c Ge W, Wei Y. Green Chem. 2012; 14: 2066
15d Chen J, Li G, Xie Y, Liao Y, Xiao F, Deng G.-J. Org. Lett. 2015; 17: 5870
15e Mal K, Kaur A, Haque F, Das I. J. Org. Chem. 2015; 80: 6400
15f Sun J.-G, Weng W.-Z, Li P, Zhang B. Green Chem. 2017; 19: 1128
15g Liang Y.-F, Yuan Y, Shen T, Song S, Jiao N. Chin. J. Chem. 2018; 36: 233
15h Mupparapu N, Khan S, Battula S, Kushwaha M, Gupta AP, Ahmed QN, Vishwakarma RA. Org. Lett. 2014; 16: 1152
15i Kohmoto S, Kobayashi T, Minami J, Ying X, Yamaguchi K, Karatsu T, Kitamura A, Kishikawa K, Yamamoto A. J. Org. Chem. 2001; 66: 66
15j Khenkin AM, Neumann R. J. Org. Chem. 2002; 67: 7075
15k Saba S, Rafique J, Braga AL. Adv. Synth. Catal. 2015; 357: 1446

16a Tomita R, Yasu Y, Koike T, Akita M. Angew. Chem. Int. Ed. 2014; 53: 7144
16b Ashikari Y, Nokami T, Yoshida J. J. Am. Chem. Soc. 2011; 133: 11840
16c Ashikari Y, Nokami T, Yoshida J. Org. Lett. 2012; 14: 938
16d Xu R, Wan J.-P, Mao H, Pan Y. J. Am. Chem. Soc. 2010; 132: 15531
16e Wu X, Gao Q, Geng X, Zhang J, Wu YD, Wu A. Org. Lett. 2016; 18: 2507
16f Xiang JC, Cheng Y, Wang M, Wu Y, Wu A. Org. Lett. 2016; 18: 4360
16g Deshidi R, Kumar M, Devari S, Shah BA. Chem. Commun. 2014; 50: 9533
16h Li X, Song S, Jiao N. Acta Chim. Sin. 2017; 75: 1202
16i Reddi RN, Prasad PK, Sudalai A. Angew. Chem. Int. Ed. 2015; 54: 14150
16j Wu X, Gao Q, Liu S. Wu A. 2014; 16: 2888
16k Song S, Huang X, Liang Y.-F, Tang C, Li X, Jiao N. Green Chem. 2015; 17: 2727
16l Gao Q, Wu X, Liu S, Wu A. Org. Lett. 2014; 16: 1732
16m Gao Q, Zhang J, Wu X, Liu S, Wu A. Org. Lett. 2015; 17: 134

17 Majetich G, Hicks R, Reister S. J. Org. Chem. 13
18 Karki M, Magolan J. J. Org. Chem. 2015; 80: 3701

19a Sayer JR, Wallden K, Pesnot T, Campbell F, Gane PJ, Simone M, Koss H, Buelens F, Boyle TP, Selwood DL, Waksman G, Tabor AB. Bioorg. Med. Chem. 2014; 22: 6459
19b Neyyappadath RM, Chisholm R, Greenhalgh MD, Rodríguez-Escrich C, Pericàs MA, Hähner G, Smith AD. ACS Catal. 2018; 8: 1067
19c Wei S, Messerer R, Tsogoeva SB. Chem. Eur. J. 2011; 17: 14380

20a Mislow K, Simmons T, Melillo J, Ternay A. J. Am. Chem. Soc. 1964; 86: 1452
20b Floyd M, Du MT, Fabio PF, Jacob LA, Johnson BD. J. Org. Chem. 1984; 50: 5022

Zusatzmaterial

Supporting Information