32.3.4.2 1-Nitrogen-Functionalized 2-Haloalkenes (Update 2020)

Abstract

This chapter is an update to the earlier Science of Synthesis contribution (Section 32.3.4) describing general synthetic methods to access 1-nitrogen-functionalized 2-haloalkenes. It puts a new focus on recent synthetic developments for this rather broad class of compounds, covering the literature from 2008 until 2018. The contents are broadly categorized by discussing methods of synthesis first, followed by specific reactivities. The synthetic methods section is arranged according to the number of substituents attached to the alkene core. Due to the vast number of examples in the literature, the current overview represents a selection of methods. In particular, when describing reactivities with 1-nitrogen-functionalized 2-haloalkenes, only archetypical examples are shown, while explicit variants are omitted.

Key words

alkenes - enamines - haloalkenes - halogenation - cross coupling - elimination reactions - Michael addition - metathesis - Wittig alkenation

• 1 Asahina Y, Iwase K, Iinuma F, Hosaka M, Ishizaki T. J. Med. Chem. 2005; 48: 3194

• 2 Banert K, Berndt C, Weigand K. Org. Lett. 2017; 19: 4900

• 3 Toriumi N, Asano N, Miyamoto K, Muranaka A, Uchiyama M. J. Am. Chem. Soc. 2018; 140: 3858

• 4 Homsi F, Rousseau G. Tetrahedron Lett. 1999; 40: 1495

• 5 Smith AB, Duffey MO, Basu K, Walsh SP, Suennemann HW, Frohn M. J. Am. Chem. Soc. 2008; 130: 422

• 6 Sashuk V, Samojłowicz C, Szadkowska A, Grela K. Chem. Commun. (Cambridge) 2008; 2468

• 7 Szudkowska-Frątczak J, Zaranek M, Hreczycho G, Kubicki M, Grabarkiewicz T, Pawluć P. Appl. Organomet. Chem. 2015; 29: 270

• 8 Pawluć P, Franczyk A, Walkowiak J, Hreczycho G, Kubicki M, Marciniec B. Org. Lett. 2011; 13: 1976

• 9 Bull JA, Mousseau JJ, Charette AB. Org. Lett. 2008; 10: 5485

• 10 Olpp T, Brückner R. Synthesis 2004; 2135

• 11 Pasqua AE, Crawford JJ, Long D.-L, Marquez R. J. Org. Chem. 2012; 77: 2149

• 12 Villa MVJ, Targett SM, Barnes JC, Whittingham WG, Marquez R. Org. Lett. 2007; 9: 1631

• 13 Anselmi E, Le TN, Bouvet S, Diter P, Pégot B, Magnier E. Eur. J. Org. Chem. 2016; 4423

• 14 Alcaide B, Almendros P, Martínez del Campo T, Naranjo T. Org. Chem. Front. 2018; 5: 817

• 15 Kirsch SF. Synthesis 2008; 3183

• 16 Romain E, Fopp C, Chemla F, Ferreira F, Jackowski O, Oestreich M, Perez-Luna A. Angew. Chem. Int. Ed. 2014; 53: 11 333

• 17 Yamagashi M, Nishigai K, Ishii A, Hata T, Urabe H. Angew. Chem. Int. Ed. 2012; 51: 6471

• 18 Yamagashi M, Nishigai K, Hata T, Urabe H. Org. Lett. 2011; 13: 4873

• 19 Xu H, Gu S, Chen W, Li D, Dou J. J. Org. Chem. 2011; 76: 2448

• 20 Liang H, Ren Z.-H, Wang Y.-Y, Guan Z.-H. Chem.–Eur. J. 2013; 19: 9789

• 21 Alonso-Cruz CR, Kennedy AR, Rodríguez MS, Suárez E. J. Org. Chem. 2008; 73: 4116

• 22 Minato A, Suzuki K, Tamao K. J. Am. Chem. Soc. 1987; 109: 1257

• 23 Torii S, Okumoto H, Tadokoro T, Nishimura A, Rashid MA. Tetrahedron Lett. 1993; 34: 2139

• 24 Couty S, Barbazanges M, Meyer C, Cossy J. Synlett 2005; 905

• 25 Brückner D. Synlett 2000; 1402

• 26 Ferreira PMT, Monteiro LS, Pereira G, Ribeiro L, Sacramento J, Silva L. Eur. J. Org. Chem. 2007; 5934

• 27 Silva NO, Abreu AS, Ferreira PMT, Monteiro LS, Queiroz M.-JRP. Eur. J. Org. Chem. 2002; 2524

• 28 Abreu AS, Ferreira PMT, Monteiro LS, Queiroz M.-JRP, Ferreira ICFR, Calhelha RC, Estevinho LM. Tetrahedron 2004; 60: 11 821

• 29 Fan Y, Zhou B, Chen K, Wang B, Li X, Xu X. Synlett 2017; 28: 1657

• 30 Gao M, Xu B. Org. Lett. 2016; 18: 4746

• 31 He G, Qiu S, Huang H, Zhu G, Zhang D, Zhang R, Zhu H. Org. Lett. 2016; 18: 1856

• 32 Compain G, Jouvin K, Martin-Mingot A, Evano G, Marrot J, Thibaudeau S. Chem. Commun. (Cambridge) 2012; 48: 5196

• 33 Lone AM, Bhat BBA. Org. Biomol. Chem. 2014; 12: 242

• 34 Chen XY, Bohmann RA, Wang L, Dong S, Räuber C, Bolm C. Chem.–Eur. J. 2015; 21: 10 330

• 35 Ji X, Huang H, Wu W, Jiang H. J. Am. Chem. Soc. 2013; 135: 5286

• 36 Li H, Li X, Zhao Z, Ma T, Sun C, Yang B. Chem. Commun. (Cambridge) 2016; 52: 10 167

• 37 Xu Z.-F, Dai H, Shan L, Li C.-Y. Org. Lett. 2018; 20: 1054

• 38 O’Brien M, Cooper D. Synlett 2016; 27: 164

• 39 Sun H, Zhang G, Zhi S, Han J, Li G, Pan Y. Org. Biomol. Chem. 2010; 8: 4236

• 40 Hlekhlai S, Samakkanad N, Sawangphon T, Pohmakotr M, Reutrakul V, Soorukram D, Jaipetch T, Kuhakarn C. Eur. J. Org. Chem. 2014; 7433

• 41 Hu Y, Yi R, Yu X, Xin X, Wang C, Wan B. Chem. Commun. (Cambridge) 2015; 51: 15 398

• 42 Leclerc MC, Gabidullin BM, Da Gama JG, Daifuku SL, Iannuzzi TE, Neidig ML, Baker RT. Organometallics 2017; 36: 849

• 43 Deutsch A, Jessen C, Deutsch C, Karaghiosoff K, Hoffmann-Röder A. Org. Lett. 2016; 18: 3474

• 44 Chen H.-X, Kang J, Chang R, Zhang Y.-L, Duan H.-Z, Li Y.-M, Chen Y.-X. Org. Lett. 2018; 20: 3278

• 45 Abreu AS, Castanheira EMS, Ferreira PMT, Monteiro LS, Pereira G, Queiroz M.-JRP. Eur. J. Org. Chem. 2008; 5697

• 46 Ricard S, Sanapo GF, Rahem N, Daoust B. J. Org. Chem. 2016; 81: 5066

• 47 Crawley ML, Goljer I, Jenkins DJ, Mehlmann JF, Nogle L, Dooley R, Mahaney PE. Org. Lett. 2006; 8: 5837

• 48 Yang J, Wang C, Xie X, Li H, Li E, Li Y. Org. Biomol. Chem. 2011; 9: 1342

• 49 Tian S, Mao Y, Jiang Y, Xu. G. Synlett 2018; 29: 949

• 50 Attanasi OA, Favi G, Filippone P, Perrulli FR, Santeusanio S. Org. Lett. 2009; 11: 309

• 51 Attanasi OA, Favi G, Filippone P, Golobič A, Perrulli FR, Stanovnik B, Svete J. Synlett 2007; 2971