Recent Advances in Exploring Diverse Decarbonylation, Decarboxylation and Desulfitation Coupling Reactions for Organic Transformations

Hongji Li; Tao Miao; Min Wang; Pinhua Li; Lei Wang

doi:10.1055/s-0035-1561388

Synlett, Inhaltsverzeichnis

Synlett 2016; 27(11): 1635-1648
DOI: 10.1055/s-0035-1561388

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Recent Advances in Exploring Diverse Decarbonylation, Decarboxylation and Desulfitation Coupling Reactions for Organic Transformations

Hongji Li

^aDepartment of Chemistry, Huaibei Normal University, Huaibei, Anhui 235000, P. R. of China

,

Tao Miao

^aDepartment of Chemistry, Huaibei Normal University, Huaibei, Anhui 235000, P. R. of China

,

Min Wang

^aDepartment of Chemistry, Huaibei Normal University, Huaibei, Anhui 235000, P. R. of China

,

Pinhua Li

^aDepartment of Chemistry, Huaibei Normal University, Huaibei, Anhui 235000, P. R. of China

,

Lei Wang*

^aDepartment of Chemistry, Huaibei Normal University, Huaibei, Anhui 235000, P. R. of China

^bState Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Shanghai 200032, P. R. of China eMail: leiwang@chnu.edu.cn

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Abstract

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Abstract

Decarbonylation, decarboxylation and desulfitation reactions have been adopted as new strategies and applied in organic synthesis for their obvious advantages over traditional cross-coupling reactions involving organometallic reagents. In this account, we highlight our recent progress on the development of novel decarbonylative, decarboxylative and desulfitative coupling reactions to construct diverse hydrocarbons via transition-metal catalysis and visible-light photoredox catalysis. In addition, mechanistic investigations describe the decarboxylative process of α-keto acids by trapping possible formed intermediates, and plausible reaction pathways are proposed. In another case, we demonstrate the successful desulfitative reactions of sulfinic acids and their sodium salts with other organic coupling partners. Among these, several reactions tolerate a range of functional groups whilst others even occur in aqueous solution.

1 Introduction

2 Palladium-Catalyzed Decarbonylative Arylation of Azoles with Arylamides

3 Transition-Metal-Catalyzed (-Mediated) Decarboxylation of Carboxylic Acids and their Derivatives

4 Visible-Light Photoredox-Catalyzed Decarboxylative Coupling Reactions

5 Transition-Metal-Catalyzed Desulfitative Coupling Reactions

6 Conclusion

Key words

decarbonylation - decarboxylation - desulfitation - transition-metal catalysis - visible-light photoredox catalysis

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Referenzen

References

For selected reviews on carboxylic acids, see:

1a Hudlicky M. Oxidations in Organic Chemistry . American Chemical Society; Washington: 1990: 105-109
1b March J. Advanced Organic Chemistry . Wiley; New York: 1992
1c Beyer H, Walter W. Lehrbuch der Organischen Chemie . Hirzel Verlag; Stuttgart: 2004. 24th ed
1d Vollhardt KP. C, Schore NE. Organische Chemie . Wiley-VCH; Weinheim: 2000. 3rd ed., S 89

For selected examples with carboxylic acids, see:

2a Ueda M, Hartwig JF. Org. Lett. 2010; 12: 92
2b Maloney K, Kuethe J, Linn K. Org. Lett. 2011; 13: 102
2c Lu Q, Zhang J, Zhao G, Qi Y, Wang H, Lei A. J. Am. Chem. Soc. 2013; 135: 11481

For sulfinic acids used as arylation reagents, see:

2d Wang G.-W, Miao T. Chem. Eur. J. 2011; 17: 5787
2e Zhou XY, Luo JY, Liu J, Peng SM, Deng G.-J. Org. Lett. 2011; 13: 1432
2f Wang H, Li Y, Zhang R, Jin K, Zhao D, Duan C. J. Org. Chem. 2012; 77: 4849

3a Goossen LJ, Rodríguez N, Goossen K. Angew. Chem. Int. Ed. 2008; 47: 3100
3b Zhou C, Liu Q, Li Y, Zhang R, Fu X, Duan C. J. Org. Chem. 2012; 77: 10468
3c Chen W, Li P, Miao T, Meng L, Wang L. Org. Biomol. Chem. 2013; 11: 420
3d Cheng K, Hu S, Zhao B, Zhang X.-M, Qi C. J. Org. Chem. 2013; 78: 5022
3e Zhao F, Tan Q, Xiao F, Zhang S, Deng G.-J. Org. Lett. 2013; 15: 1520
3f Sévigny S, Forgione P. Chem. Eur. J. 2013; 19: 2256

4a Goossen LJ, Ghosh K. Chem. Commun. 2001; 2084
4b Goossen LJ, Döhring A. Adv. Synth. Catal. 2003; 345: 943
4c Goossen LJ, Paetzold J, Winkel L. Synlett 2002; 1721
4d Goossen LJ, Paetzold J. Angew. Chem. Int. Ed. 2004; 43: 1095
4e Liu J, Zhou XY, Rao HH, Xiao FH, Li C.-J, Deng G.-J. Chem. Eur. J. 2011; 17: 7996
4f Miao T, Wang G.-W. Chem. Commun. 2011; 47: 9501
4g Yao H, Yang L, Shuai Q, Li C.-J. Adv. Synth. Catal. 2011; 353: 1701
4h Behrends M, Sörmarker J, Sjöberg P, Larhed M. ACS Catal. 2011; 1: 1455
4i Liu B, Guo Q, Cheng Y, Lan J, You J. Chem. Eur. J. 2011; 17: 13415
4j Wu M, Luo J, Xiao F, Zhang S, Deng G.-J, Luo H.-A. Adv. Synth. Catal. 2012; 354: 335

5a Patureau FW, Glorius F. Angew. Chem. Int. Ed. 2011; 50: 1977
5b Guimond N, Gorelsky SI, Fagnou K. J. Am. Chem. Soc. 2011; 133: 6449

6 Li C, Li P, Yang J, Wang L. Chem. Commun. 2012; 48: 4214

7a Myers AG, Tanaka D, Mannion MR. J. Am. Chem. Soc. 2002; 124: 11250
7b Tanaka D, Romeril SP, Myers AG. J. Am. Chem. Soc. 2005; 127: 10323

8a Yin L, Kanai M, Shibasaki M. J. Am. Chem. Soc. 2009; 131: 9610
8b Duan Z, Ranjit S, Zhang P, Liu X. Chem. Eur. J. 2009; 15: 3666
8c Hu J, Zhao N, Yang B, Wang G, Guo L, Liang Y, Yang S. Chem. Eur. J. 2011; 17: 5516
8d Zhang Y, Jamison TF, Patel S, Mainolfi N. Org. Lett. 2011; 13: 280
8e Feng Q, Song Q. Adv. Synth. Catal. 2014; 356: 1697
8f Sun Z, Zhang J, Zhao P. Org. Lett. 2010; 12: 992
8g Neely JM, Rovis T. J. Am. Chem. Soc. 2014; 136: 2735
8h Yang K, Zhang C, Wang P, Zhang Y, Ge H.-B. Chem. Eur. J. 2014; 20: 7241
8i Zhang F, Greaney MF. Org Lett. 2010; 12: 4745
8j Hwang J, Park K, Choe J, Min H, Song KH, Lee S. J. Org. Chem. 2014; 79: 3267

9 Li H, Li P, Wang L. Org. Lett. 2013; 15: 620
10 Li H, Li P, Tan H, Wang L. Chem. Eur. J. 2013; 19: 14432
11 Li H, Li P, Zhao Q, Wang L. Chem. Commun. 2013; 49: 9170
12 Li D, Wang M, Liu J, Zhao Q, Wang L. Chem. Commun. 2013; 49: 3640
13 Yu L, Li P, Wang L. Chem. Commun. 2013; 49: 2368

14a North M In Science of Synthesis . Vol. 19. Murahashi S.-I. Thieme; Stuttgart: 2004: 235
14b Breuer M, Ditrich K, Habicher T, Hauer B, Kebler M, Stürmer R, Zelinski T. Angew. Chem. Int. Ed. 2004; 43: 788

15 Chen L, Li H, Yu F, Wang L. Chem. Commun. 2014; 50: 14866
16 Tan H, Li H, Wang J, Wang L. Chem. Eur. J. 2015; 21: 1904
17 Li D, Xu N, Zhang Y, Wang L. Chem. Commun. 2014; 50: 14862

18a Kalyani D, McMurtrey KB, Neufeldt SR, Sanford MS. J. Am. Chem. Soc. 2011; 133: 18566
18b Ye Y, Sanford MS. J. Am. Chem. Soc. 2012; 134: 9034
18c Sahoo B, Hopkinson MN, Glorius F. J. Am. Chem. Soc. 2013; 135: 5505
18d Zuo Z, Ahneman DT, Chu L, Terrett JA, Doyle AG, MacMillan DW. C. Science 2014; 345: 437
18e Tellis JC, Primer DN, Molander GA. Science 2014; 345: 433
18f Zoller J, Fabry DC, Ronge MA, Rueping M. Angew. Chem. Int. Ed. 2014; 53: 13264
18g Shu X.-Z, Zhang M, He Y, Frei H, Dean Toste F. J. Am. Chem. Soc. 2014; 136: 5844
18h Terrett JA, Cuthbertson JD, Shurtleff VW, MacMillan DW. C. Nature 2015; 524: 330
18i Fabry DC, Ronge MA, Zoller J, Rueping M. Angew. Chem. Int. Ed. 2015; 54: 2801
18j Xuan J, Zeng T.-T, Feng Z.-J, Deng Q.-H, Chen J.-R, Lu L.-Q, Xiao W.-J, Alper H. Angew. Chem. Int. Ed. 2015; 54: 1625

19 Zhou C, Li P, Zhu X, Wang L. Org. Lett. 2015; 17: 6198
20 Xu N, Li P, Xie Z, Wang L. Chem. Eur. J. 2016; 22: 2236
21 Zhdankin VV, Stang PJ. Chem. Rev. 2008; 108: 5299 ; and references cited therein
22 Tan H, Li H, Ji W, Wang L. Angew. Chem. Int. Ed. 2015; 54: 8374

23a Fan J.-H, Wei W.-T, Zhou M.-B, Song R.-J, Li J.-H. Angew. Chem. Int. Ed. 2014; 53: 6650
23b Xie J, Xu P, Li H, Xue Q, Jin H, Cheng Y, Zhu C. Chem. Commun. 2013; 49: 5672
23c Dai Q, Yu J, Jiang Y, Guo S, Yang H, Cheng J. Chem. Commun. 2014; 50: 3865
23d Matcha K, Narayan R, Antonchick AP. Angew. Chem. Int. Ed. 2013; 52: 7985
23e Li Y.-M, Sun M, Wang H.-L, Tian Q.-P, Yang S.-D. Angew. Chem. Int. Ed. 2013; 52: 3972

24 Ji W, Tan H, Li P, Wang M, Wang L. Chem. Commun. 2016; 52: 1462
25 Heck RF. Acc. Chem. Res. 1979; 12: 146
26 Miyaura N, Suzuki A. Chem. Rev. 1995; 95: 2457
27 King AO, Okukado N, Negishi E.-i. J. Chem. Soc., Chem. Commun. 1977; 683
28 Miao T, Li P, Wang G.-W, Wang L. Chem. Asian J. 2013; 8: 3185
29 Miao T, Wang L. Adv. Synth. Catal. 2014; 356: 429
30 Miao T, Wang L. Adv. Synth. Catal. 2014; 356: 967