Halogen Bonding II pp 167-203 | Cite as
Halogen Bonds in Organic Synthesis and Organocatalysis
Abstract
In contrast to hydrogen bonding, halogen bonding has so far found very little use in organic synthesis and organocatalysis. Although there are multiple reports on the use of elemental iodine in a wide range of organic reactions, the understanding of the actual mode of activation in these cases is very rudimentary. Recently, first proof-of-principle reactions have been established towards the use of carbon-based halogen-bond donors as activators or organocatalysts. These halogen-based Lewis acids offer more structural variety and potential than elemental iodine itself, and the mode of activation is better understood. Yet, the reported cases still only cover simple benchmark reactions, and there is a clear need for further and more complex applications.
Keywords
Halogen bonding Noncovalent interactions Organocatalysis Supramolecular chemistryReferences
- 1.Jeffrey GA (1997) An introduction to hydrogen bonding. Oxford University Press, OxfordGoogle Scholar
- 2.Steed JW, Atwood JL (2009) Supramolecular chemistry, 2nd edn. Wiley, ChichesterGoogle Scholar
- 3.Pihko PM (ed) (2009) Hydrogen bonding in organic synthesis. Wiley, WeinheimGoogle Scholar
- 4.Gholami MR, Talebi BA (2003) J Phys Org Chem 16:79–83Google Scholar
- 5.Blake JF, Jorgensen WL (1991) J Am Chem Soc 113:7430–7432Google Scholar
- 6.Blake JF, Lim D, Jorgensen WL (1994) J Org Chem 59:803–805Google Scholar
- 7.Hine J, Linden SM, Kanagasabapathy VM (1985) J Am Chem Soc 107:1082–1083Google Scholar
- 8.Kelly TR, Meghani P, Ekkundi VS (1990) Tetrahedron Lett 31:3381–3384Google Scholar
- 9.Etter MC, Panunto TW (1988) J Am Chem Soc 110:5896–5897Google Scholar
- 10.Etter MC (1990) Acc Chem Res 23:120–126Google Scholar
- 11.Curran DP, Kuo LH (1994) J Org Chem 59:3259–3261Google Scholar
- 12.Curran DP, Kuo LH (1995) Tetrahedron Lett 36:6647–6650Google Scholar
- 13.Schreiner PR (2003) Chem Soc Rev 32:289–296Google Scholar
- 14.Zhang Z, Schreiner PR (2009) Chem Soc Rev 38:1187–1198Google Scholar
- 15.Doyle AG, Jacobsen EN (2007) Chem Rev 107:5713–5743Google Scholar
- 16.Wittkopp A, Schreiner PR (2003) Chem Eur J 9:407–414Google Scholar
- 17.Sigman MS, Jacobsen EN (1998) J Am Chem Soc 120:4901–4902Google Scholar
- 18.Vachal P, Jacobsen EN (2002) J Am Chem Soc 124:10012–10014Google Scholar
- 19.Zuend SJ, Jacobsen EN (2009) J Am Chem Soc 131:15358–15374Google Scholar
- 20.Mahlau M, List B (2013) Angew Chem Int Ed 52:518–533Google Scholar
- 21.Brak K, Jacobsen EN (2013) Angew Chem Int Ed 52:534–561Google Scholar
- 22.Beckendorf S, Asmus S, Mancheno OG (2012) ChemCatChem 4:926–936Google Scholar
- 23.Raheem IT, Thiara PS, Peterson EA, Jacobsen EN (2007) J Am Chem Soc 129:13404–13405Google Scholar
- 24.Taylor MS, Jacobsen EN (2006) Angew Chem Int Ed 45:1520–1543Google Scholar
- 25.Malerich JP, Hagihara K, Rawal VH (2008) J Am Chem Soc 130:14416–14417Google Scholar
- 26.Metrangolo P, Meyer F, Pilati T, Resnati G, Terraneo G (2008) Angew Chem Int Ed 47:6114–6127Google Scholar
- 27.Hassel O, Roemming C (1962) Quart Rev 16:1–18Google Scholar
- 28.Bent HA (1968) Chem Rev 68:587–648Google Scholar
- 29.Fourmigue M (2009) Curr Opin Solid State Mater Sci 13:36–45Google Scholar
- 30.Legon AC (2010) Phys Chem Chem Phys 12:7736–7747Google Scholar
- 31.Lu Y, Wang Y, Zhu W (2010) Phys Chem Chem Phys 12:4543–4551Google Scholar
- 32.Desiraju GR, Ho PS, Kloo L, Legon AC, Marquardt R, Metrangolo P, Politzer P, Resnati G, Rissanen K (2013) Pure Appl Chem 85:1711–1713Google Scholar
- 33.Corradi E, Meille SV, Messina MT, Metrangolo P, Resnati G (2000) Angew Chem Int Ed 39:1782–1786Google Scholar
- 34.Weiss R, Miess GE, Haller A, Reinhardt W (1986) Angew Chem Int Ed 25:103–104Google Scholar
- 35.Legon AC (1999) Angew Chem Int Ed 38:2687–2714Google Scholar
- 36.Kilah NL, Wise MD, Serpell CJ, Thompson AL, White NG, Christensen KE, Beer PD (2010) J Am Chem Soc 132:11893–11895Google Scholar
- 37.Vargas Jentzsch A, Emery D, Mareda J, Metrangolo P, Resnati G, Matile S (2011) Angew Chem Int Ed 50:11675–11678Google Scholar
- 38.Hardegger LA, Kuhn B, Spinnler B, Anselm L, Ecabert R, Stihle M, Gsell B, Thoma R, Diez J, Benz J, Plancher J-M, Hartmann G, Banner DW, Haap W, Diederich F (2011) Angew Chem Int Ed 50:314–318Google Scholar
- 39.Carlsson A-CC, Graefenstein J, Budnjo A, Laurila JL, Bergquist J, Karim A, Kleinmaier R, Brath U, Erdelyi M (2012) J Am Chem Soc 134:5706–5715Google Scholar
- 40.Raatikainen K, Rissanen K (2012) Chem Sci 3:1235–1239Google Scholar
- 41.Meazza L, Foster JA, Fucke K, Metrangolo P, Resnati G, Steed JW (2013) Nat Chem 5:42–47Google Scholar
- 42.Mele A, Metrangolo P, Neukirch H, Pilati T, Resnati G (2005) J Am Chem Soc 127:14972–14973Google Scholar
- 43.Sarwar MG, Dragisic B, Sagoo S, Taylor MS (2010) Angew Chem Int Ed 49:1674–1677Google Scholar
- 44.Dimitrijevic E, Kvak O, Taylor MS (2010) Chem Commun 46:9025–9027Google Scholar
- 45.Caballero A, White NG, Beer PD (2011) Angew Chem Int Ed 50:1845–1848Google Scholar
- 46.Zapata F, Caballero A, White NG, Claridge TDW, Costa PJ, Felix V, Beer PD (2012) J Am Chem Soc 134:11533–11541Google Scholar
- 47.Huber SM, Jimenez-Izal E, Ugalde JM, Infante I (2012) Chem Commun 48:7708–7710Google Scholar
- 48.Sarwar MG, Dragisic B, Salsberg LJ, Gouliaras C, Taylor MS (2010) J Am Chem Soc 132:1646–1653Google Scholar
- 49.Cabot R, Hunter CA (2005–2007) Chem Commun 2009Google Scholar
- 50.Laurence C, Graton J, Berthelot M, El Ghomari MJ (2011) Chem Eur J 17:10431–10444Google Scholar
- 51.Politzer P, Murray JS, Clark T (2010) Phys Chem Chem Phys 12:7748–7757Google Scholar
- 52.Clark T (2013) Wiley Interdiscip Rev Comput Mol Sci 3:13–20Google Scholar
- 53.Karpfen A (2003) Theor Chem Acc 110:1–9Google Scholar
- 54.Hassel O (1970) Science 170:497–502Google Scholar
- 55.Weiss R, Rechinger M, Hampel F (1994) Angew Chem Int Ed 1893–1995Google Scholar
- 56.Weiss R, Schwab O, Hampel F (1999) Chem Eur J 5:968–974Google Scholar
- 57.Huber SM, Scanlon JD, Jimenez-Izal E, Ugalde JM, Infante I (2013) Phys Chem Chem Phys 15:10350–10357Google Scholar
- 58.Rissanen K (2008) CrystEngComm 10:1107–1113Google Scholar
- 59.Brammer L, Espallargas GM, Libri S (2008) CrystEngComm 10:1712–1727Google Scholar
- 60.Bertani R, Sgarbossa P, Venzo A, Lelj F, Amati M, Resnati G, Pilati T, Metrangolo P, Terraneo G (2010) Coord Chem Rev 254:677–695Google Scholar
- 61.Cavallo G, Metrangolo P, Pilati T, Resnati G, Sansotera M, Terraneo G (2010) Chem Soc Rev 39:3772–3783Google Scholar
- 62.Di Paolo T, Sandorfy C (1974) Can J Chem 52:3612–3622Google Scholar
- 63.Erdelyi M (2012) Chem Soc Rev 41:3547–3557Google Scholar
- 64.Beale TM, Chudzinski MG, Sarwar MG, Taylor MS (2013) Chem Soc Rev 42:1667–1680Google Scholar
- 65.Vargas Jentzsch A, Matile S (2013) J Am Chem Soc 135:5302–5303Google Scholar
- 66.Vargas Jentzsch A, Emery D, Mareda J, Nayak SK, Metrangolo P, Resnati G, Sakai N, Matile S (2012) Nat Commun 3:905Google Scholar
- 67.Pearson RG (1963) J Am Chem Soc 85:3533–3539Google Scholar
- 68.Mayr H, Breugst M, Ofial AR (2011) Angew Chem Int Ed 50:6470–6505Google Scholar
- 69.Zefirov NS, Makhon’kov DI (1982) Chem Rev 82:615–624Google Scholar
- 70.Bailey WF, Patricia JJ (1988) J Organomet Chem 352:1–46Google Scholar
- 71.Wittig G, Schollkopf U (1958) Tetrahedron 3:91–93Google Scholar
- 72.Wittig G (1958) Angew Chem Int Ed 70:65–71Google Scholar
- 73.Reich HJ, Phillips NH, Reich IL (1985) J Am Chem Soc 107:4101–4103Google Scholar
- 74.Reich HJ, Green DP, Phillips NH (1989) J Am Chem Soc 111:3444–3445Google Scholar
- 75.Perkins CW, Martin JC, Arduengo AJ, Lau W, Alegria A, Kochi JK (1980) J Am Chem Soc 102:7753–7759Google Scholar
- 76.Farnham WB, Calabrese JC (1986) J Am Chem Soc 108:2449–2451Google Scholar
- 77.Schulze V, Bronstrup M, Bohm VPW, Schwerdtfeger P, Schimeczek M, Hoffmann RW (1998) Angew Chem Int Ed 37:824–826Google Scholar
- 78.Hoffmann RW, Broenstrup M, Mueller M (2003) Org Lett 5:313–316Google Scholar
- 79.Metrangolo P, Pilati T, Resnati G (2006) CrystEngComm 8:946–947Google Scholar
- 80.Dumas JM, Peurichard H, Gomel M (1978) J Chem Res (S) 54–55Google Scholar
- 81.Legon AC (1998) Chem Eur J 4:1890–1897Google Scholar
- 82.Rosokha SV, Kochi JK (2002) J Org Chem 67:1727–1737Google Scholar
- 83.Hassel O, Stromme KO (1958) Acta Chem Scand 12:1146Google Scholar
- 84.Hassel O, Stroemme KO (1959) Acta Chem Scand 13:1781–1786Google Scholar
- 85.Vasilyev AV, Lindeman SV, Kochi JK (2001) Chem Commun 909–910Google Scholar
- 86.Banerjee AK, Vera W, Mora H, Laya MS, Bedoya L, Cabrera EV (2006) J Sci Ind Res 65:299–308Google Scholar
- 87.Togo H, Iida S (2006) Synlett 2159–2175Google Scholar
- 88.Jereb M, Vrazic D, Zupan M (2011) Tetrahedron 67:1355–1387Google Scholar
- 89.Banik BK, Fernandez M, Alvarez C (2005) Tetrahedron Lett 46:2479–2482Google Scholar
- 90.Yadav JS, Reddy BVS, Reddy MS, Prasad AR (2002) Tetrahedron Lett 43:9703–9706Google Scholar
- 91.Das B, Chowdhury N, Damodar K (2007) Tetrahedron Lett 48:2867–2870Google Scholar
- 92.Das B, Balasubramanyam P, Krishnaiah M, Veeranjaneyulu B, Reddy GC (2009) Synthesis 3467–3471Google Scholar
- 93.Reddy BVS, Divyavani C, Yadav JS (2010) Synthesis 1617–1620Google Scholar
- 94.Das B, Kumar JN, Kumar AS, Kanth BS (2010) Synthesis 3113–3116Google Scholar
- 95.Boens B, Faugeras P-A, Vergnaud J, Lucas R, Teste K, Zerrouki R (2010) Tetrahedron 66:1994–1996Google Scholar
- 96.Batchu H, Bhattacharyya S, Batra S (2012) Org Lett 14:6330–6333Google Scholar
- 97.Singh N, Singh KN (2012) Synlett 23:2116–2120Google Scholar
- 98.Xu W, Kloeckner U, Nachtsheim BJ (2013) J Org Chem 78:6065–6074Google Scholar
- 99.Rai VK, Sharma N, Kumar A (2013) Synlett 24:97–101Google Scholar
- 100.Chen D-S, Li Y-L, Liu Y, Wang X-S (2013) Tetrahedron 69:7045–7050Google Scholar
- 101.Bhunia N, Das B (2013) Synthesis 45:1045–1050Google Scholar
- 102.Figueiredo CAM, Reddy KRKK, Monteiro PA, de Carvalho JE, Ruiz ALTG, Silva LF Jr (2013) Synthesis 45:1076–1082Google Scholar
- 103.Yan R, Kang X, Zhou X, Li X, Liu X, Xiang L, Li Y, Huang G (2014) J Org Chem 79:465–470Google Scholar
- 104.Huang H-M, Li Y-J, Ye Q, Yu W-B, Han L, Jia J-H, Gao J-R (2014) J Org Chem 79:1084–1092Google Scholar
- 105.Das S, Borah R, Devi RR, Thakur AJ (2008) Synlett 2741–2762Google Scholar
- 106.Bandgar BP, Shaikh KA (2003) Tetrahedron Lett 44:1959–1961Google Scholar
- 107.Parvatkar PT, Parameswaran PS, Tilve SG (2012) Chem Eur J 18:5460–5489Google Scholar
- 108.Alcaide B, Almendros P, Cabrero G, Ruiz MP (2008) Synthesis 2835–2839Google Scholar
- 109.Cruickshank FR, Benson SW (1969) J Phys Chem 73:733–737Google Scholar
- 110.Silva LF Jr, Quintiliano SA (2009) Tetrahedron Lett 50:2256–2260Google Scholar
- 111.Yang F-L, Wang F-X, Wang T-T, Wang Y-J, Tian S-K (2014) Chem Commun 50:2111–2113Google Scholar
- 112.Coulembier O, Meyer F, Dubois P (2010) Polym Chem 1:434–437Google Scholar
- 113.Holleman A, Wiberg N (2007) Lehrbuch der Anorganischen Chemie, 102nd edn. de Gruyter, Berlin, p 461Google Scholar
- 114.Bew SP, Fairhurst SA, Hughes DL, Legentil L, Liddle J, Pesce P, Nigudkar S, Wilson MA (2009) Org Lett 11:4552–4555Google Scholar
- 115.Metrangolo P, Murray JS, Pilati T, Politzer P, Resnati G, Terraneo G (2011) Cryst Growth Des 11:4238–4246Google Scholar
- 116.Virgil SC (1995) In: Paquette LA (ed) Encyclopedia of reagents for organic synthesis. Wiley, New York, p 768Google Scholar
- 117.Fieser LF, Fieser M (1998) Reagents for organic synthesis 12. Wiley, New York, p 79Google Scholar
- 118.Wei Y, Lin S, Liang F (2012) Org Lett 14:4202–4205Google Scholar
- 119.Wei Y, Lin S, Liang F, Zhang J (2013) Org Lett 15:852–855Google Scholar
- 120.Wei Y, Liang F, Zhang X (2013) Org Lett 15:5186–5189Google Scholar
- 121.Castellote I, Moron M, Burgos C, Alvarez-Builla J, Martin A, Gomez-Sal P, Vaquero JJ (2007) Chem Commun 1281–1283Google Scholar
- 122.Denmark SE, Kuester WE, Burk MT (2012) Angew Chem Int Ed 51:10938–10953Google Scholar
- 123.Sakakura A, Ukai A, Ishihara K (2007) Nature 445:900–903Google Scholar
- 124.Bruckmann A, Pena MA, Bolm C (2008) Synlett 900–902Google Scholar
- 125.Zhou Y-G (2007) Acc Chem Res 40:1357–1366Google Scholar
- 126.Metrangolo P, Panzeri W, Recupero F, Resnati G (2002) J Fluorine Chem 114:27–33Google Scholar
- 127.Gladysz JA (1994) Science 266:55–56Google Scholar
- 128.Dordonne S, Crousse B, Bonnet-Delpon D, Legros J (2011) Chem Commun 47:5855–5857Google Scholar
- 129.Lindsay VNG, Lin W, Charette AB (2009) J Am Chem Soc 131:16383–16385Google Scholar
- 130.Walter SM, Kniep F, Herdtweck E, Huber SM (2011) Angew Chem Int Ed 50:7187–7191Google Scholar
- 131.Bondi A (1964) J Phys Chem 68:441–451Google Scholar
- 132.Walter SM, Kniep F, Rout L, Schmidtchen FP, Herdtweck E, Huber SM (2012) J Am Chem Soc 134:8507–8512Google Scholar
- 133.Kniep F, Jungbauer SH, Zhang Q, Walter SM, Schindler S, Schnapperelle I, Herdtweck E, Huber SM (2013) Angew Chem Int Ed 52:7028–7032Google Scholar
- 134.Beweries T, Brammer L, Jasim NA, McGrady JE, Perutz RN, Whitwood AC (2011) J Am Chem Soc 133:14338–14348Google Scholar
- 135.Libri S, Jasim NA, Perutz RN, Brammer L (2008) J Am Chem Soc 130:7842–7844Google Scholar
- 136.Kniep F, Walter SM, Herdtweck E, Huber SM (2012) Chem Eur J 18:1306–1310Google Scholar
- 137.Freytag M, Jones PG, Ahrens B, Fischer AK (1999) New J Chem 23:1137–1139Google Scholar
- 138.Brammer L, Espallargas GM, Adams H (2003) CrystEngComm 5:343–345Google Scholar
- 139.Logothetis TA, Meyer F, Metrangolo P, Pilati T, Resnati G (2004) New J Chem 28:760–763Google Scholar
- 140.Espallargas GM, Brammer L, Sherwood P (2006) Angew Chem Int Ed 45:435–440Google Scholar
- 141.Awwadi FF, Willett RD, Twamley B (2009) J Mol Struct 918:116–122Google Scholar
- 142.Minguez Espallargas G, Zordan F, Arroyo Marin L, Adams H, Shankland K, van de Streek J, Brammer L (2009) Chem Eur J 15:7554–7568Google Scholar
- 143.Raatikainen K, Cametti M, Rissanen K (2010) Beilstein J Org Chem 6(4)Google Scholar
- 144.Kniep F, Rout L, Walter SM, Bensch HKV, Jungbauer SH, Herdtweck E, Huber SM (2012) Chem Commun 48:9299–9301Google Scholar
- 145.Hein JE, Tripp JC, Krasnova LB, Sharpless KB, Fokin VV (2009) Angew Chem Int Ed 48:8018–8021Google Scholar
- 146.Kilah NL, Wise MD, Beer PD (2011) Cryst Growth Des 11:4565–4571Google Scholar
- 147.Mullen KM, Mercurio J, Serpell CJ, Beer PD (2009) Angew Chem Int Ed 48:4781–4784Google Scholar
- 148.Walter SM, Jungbauer SH, Kniep F, Schindler S, Herdtweck E, Huber SM (2013) J Fluorine Chem 150:14–20Google Scholar
- 149.Tannaci JF, Noji M, McBee JL, Tilley TD (2008) J Org Chem 73:7895–7900Google Scholar
- 150.Olah GA, Wang Q, Sandford G, Surya Prakash GK (1993) J Org Chem 58:3194–3195Google Scholar
- 151.Reisman SE, Doyle AG, Jacobsen EN (2008) J Am Chem Soc 130:7198–7199Google Scholar
- 152.Jungbauer SH, Walter SM, Schindler S, Rout L, Kniep F, Huber SM (2014) Activation of a carbonyl compound by halogen bonding. Chem Commun 50:6281–6284Google Scholar