Ecofriendly Oxidative Nuclear
Halogenation of Aromatic Compounds Using Potassium and Ammonium
Halides

V. V. Krishna Mohan Kandepi; Nama Narender

doi:10.1055/s-0031-1289620

Subscribe to RSS

Please copy the URL and add it into your RSS Feed Reader.

https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000084.xml

Share / Bookmark

Facebook X Linkedin Weibo

Download PDF

Synthesis 2012(1): 15-26
DOI: 10.1055/s-0031-1289620

REVIEW

Ecofriendly Oxidative Nuclear Halogenation of Aromatic Compounds Using Potassium and Ammonium Halides

V. V. Krishna Mohan Kandepi, Nama Narender*
Catalysis Group, Indian Institute of Chemical Technology, Uppal Road, Tarnaka, Hyderabad 500607, India
Fax: +91(40)27160387; Fax: +91(40)27160757; e-Mail: narendern33@yahoo.co.in;

Further Information

Publication History

Received 27 September 2011
Publication Date:
24 November 2011 (online)

Abstract
Full Text
References

Permissions and Reprints All articles of this category

Abstract

Halogenated aromatic compounds are versatile building blocks in organic synthesis and form an important class of molecules in organic chemistry. A wide variety of methods and reagent systems have been developed to affect their synthesis. This short review presents an overview of methods used for efficient and regioselective nuclear halogenation of activated aromatic compounds with potassium and ammonium halides.

1 Introduction

2 Chlorination

2.1 Oxidative Chlorination with Potassium Chloride

2.2 Oxidative Chlorination with Ammonium Chloride

3 Bromination

3.1 Oxidative Bromination with Potassium Bromide

3.2 Oxidative Bromination with Ammonium Bromide

4 Iodination

4.1 Oxidative Iodination with Potassium Iodide

4.2 Oxidative Iodination with Ammonium Iodide

5 Conclusions

Key words

halogenation - aromatic compounds - regioselectivity - potassium halides - ammonium halides - atom economy - environmentally benign

References

1a Normat H. Adv. Org. Chem. 1960, 2: 1

Google Scholar
1b Wakefield BJ. The Chemistry of Organolithium Compounds Pergamon; Oxford: 1976.

Google Scholar
1c Davies SG. In Organotransition Metal Chemistry, Applications to Organic Synthesis Pergamon; Oxford: 1982.

Google Scholar
1d Cannon KC. Krow GR. In Handbook of Grignard Reagents Silverman GS. Rakita PE. M. Dekker; NewYork: 1996. Chap. 26. p.527

Google Scholar
2 Shaw PD. Hager LP. J. Am. Chem. Soc. 1959, 81: 6527

Google Scholar
3a Larock RC. Comprehensive Organic Transformations VCH; New York: 1989.

Google Scholar
3b De la Mare PBD. Electrophilic Halogenation Cambridge University Press; Cambridge: 1976.

Google Scholar
3c Dear KM. Top. Curr. Chem. 1993, 164: 115

Google Scholar
4a Clark BF. Chem. News 1931, 143: 265

Google Scholar
4b Ginsburg D. J. Am. Chem. Soc. 1951, 73: 2723

Google Scholar
4c Zimmer H. Audrieth LF. J. Am. Chem. Soc. 1954, 76: 3856

Google Scholar
4d Walling C. Mintz MJ. J. Am. Chem. Soc. 1967, 89: 1515

Google Scholar
4e Tanner DD. Gidley GC. J. Am. Chem. Soc. 1968, 90: 808

Google Scholar
4f Moore HW. Gajipe G. Synthesis 1973, 49

Google Scholar
4g Watson WD. J. Org. Chem. 1974, 39: 1160

Google Scholar
4h Duggan AJ. Hall SS. J. Org. Chem. 1977, 42: 1057

Google Scholar
4i Sato W. Ikeda N. Yamamoto H. Chem. Lett. 1982, 141

Google Scholar
4j Ravindranath B. Srinivas P. Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem. 1985, 24: 163

Google Scholar
4k Peake CJ. Strickland JH. Synth. Commun. 1986, 16: 763

Google Scholar
4l Raja R. Ratna Samy P. J. Catal. 1997, 170: 244

Google Scholar
4m Baumgarten HE. Bower FA. J. Am. Chem. Soc. 1954, 76: 4561

Google Scholar
4n Baumgarten HE. Petersen JM. Org. Synth. 1961, 41: 82

Google Scholar
4o Bucciarelli M. Forui A. Moretti I. Torre G. J. Org. Chem. 1983, 48: 2640

Google Scholar
4p Grob CA. Schmid HJ. Helv. Chim. Acta 1953, 36: 1763

Google Scholar
4q Walling C. Mintz MJ. J. Org. Chem. 1967, 32: 1286

Google Scholar
4r Detty MR. J. Org. Chem. 1980, 45: 274

Google Scholar
5 Koini EN. Avlonitis N. Calogeropoulou T. Synlett 2011, 1537

Google Scholar
6a Barhate NB. Gajare AS. Wakharkar RD. Bedekar AV. Tetrahedron Lett. 1998, 39: 6349

Google Scholar
6b Chung KH. Kim KM. Kim JN. Ryu EK. Synth. Commun. 1991, 21: 1917

Google Scholar
6c Chung KH. Kim HJ. Kim HR. Ryu EK. Synth. Commun. 1990, 20: 2991

Google Scholar
6d Dakka J. Sassan Y. J. Chem. Soc., Chem. Commun. 1987, 1421

Google Scholar
6e Lubbecke H. Boldt P. Tetrahedron 1978, 34: 1577

Google Scholar
7a For oxidative halogenations with green oxidants see: Podgorsek A. Zupan M. Iskra J. Angew. Chem. Int. Ed. 2009, 48: 8424

Google Scholar
7b Peroxide Chemistry: Mechanistic and Preparative Aspects of Oxygen Transfer Wiley-VCH; Weinheim: 2000.

Google Scholar
8a Higgs DE. Nelen MI. Detty MR. Org. Lett. 2001, 3: 349

Google Scholar
8b Sels B. De Vos D. Buntinx M. Pierard F. Mesmaeker AK.-D. Jacobs P. Nature 1999, 400: 855

Google Scholar
9 Pravst I. Zupan M. Stavber S. Curr. Org. Chem. 2009, 13: 47

Google Scholar
10a Taylor SD. Kotoris CC. Hum G. Tetrahedron 1999, 55: 12431

Google Scholar
10b Houben-Weyl 4th ed., Vol. E10: Baasner B. Hagemann H. Tatlow JC. Thieme; Stuttgart: 1999.

Google Scholar
10c Modern Organofluorine Chemistry — Synthetic Aspects, In Advances in Organic Synthesis Vol. 2: Rahman A. Laali KK. Bentham Science Publishers Ltd.; Hilversum: 2006.

Google Scholar
12a Konishi H. Aritomi K. Okano V. Kiji J. Bull. Chem. Soc. Jpn. 1989, 62: 591

Google Scholar
12b Bovonsombat P. McNelis E. Synthesis 1993, 237

Google Scholar
12c Smith K. Bahzad D. Chem. Commun. 1996, 467

Google Scholar
12d Paul V. Sudalai A. Daniel T. Srinivasan KV. Tetrahedron Lett. 1994, 35: 7055

Google Scholar
12e Auerbach J. Weissman SA. Blacklock V. Angeless MR. Hoogsteen K. Tetrahedron Lett. 1993, 34: 931

Google Scholar
12f Oberhauser T. J. Org. Chem. 1997, 62: 4504

Google Scholar
12g Singh AP. Mirajkar SP. Sharma S. J. Mol. Catal. A: Chem. 1999, 150: 241

Google Scholar
12h Goldberg Y. Alper H. J. Mol. Catal. A: Chem. 1994, 88: 377

Google Scholar
12i Srivastava SK. Chauhan PMS. Bhaduri AP. Chem. Commun. 1996, 2679

Google Scholar
13 Taylor R. Electrophilic Aromatic Substitution Wiley; Chichester: 1990. p.362

Google Scholar
14 Holderich W. Hesse M. Naumann F. Angew. Chem., Int. Ed. Engl. 1988, 27: 226

Google Scholar
15a Neumann R. Assael I. J. Chem. Soc., Chem. Commun. 1988, 1285

Google Scholar
15b Bogdal D. Lukasiewicz M. Pielichowski J. Green Chem. 2004, 6: 110

Google Scholar
16 Narender N. Srinivasu P. Kulkarni SJ. Raghavan KV. Synth. Commun. 2002, 32: 279

Google Scholar
17 Webb KS. Levy D. Tetrahedron Lett. 1995, 36: 5117 ; and references cited therein

Google Scholar
18a Ford-Smith MH. Habeeb JJ. J. Chem. Soc. D 1969, 1445

Google Scholar
18b Ford-Smith MH. Habeeb JJ. J. Chem. Soc., Dalton Trans. 1973, 461

Google Scholar
19 Muathen HA. Helv. Chim. Acta 2003, 86: 164

Google Scholar
20 Narender N. Krishna Mohan KVV. Srinivasu P. Kulkarni SJ. Raghavan KV. Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem. 2004, 43: 1335

Google Scholar
21 Narender N. Srinivasu P. Ramakrishna Prasad M. Kulkarni SJ. Raghavan KV. Synth. Commun. 2002, 32: 2313

Google Scholar
22 Dinesh CU. Kumar R. Pandey B. Kumar P. J. Chem. Soc., Chem. Commun. 1995, 611

Google Scholar
23 Maurya MR. Saklani H. Agarwal S. Catal. Commun. 2004, 563

Google Scholar
24 Choudary BM. Sudha Y. Reddy PN. Synlett 1994, 450

Google Scholar
25a Mallick S. Parida KM. Catal. Commun. 2007, 889

Google Scholar
25b Mallick S. Parida KM. Dash SS. J. Mol. Catal. A: Chem. 2007, 261: 172

Google Scholar
26 Walker JV. Morey M. Carlson H. Davidson A. Stucky GD. Butler A. J. Am. Chem. Soc. 1997, 119: 6921

Google Scholar
27 Das DP. Parida KM. J. Mol. Catal. A: Chem. 2006, 253: 70

Google Scholar
28 Das DP. Parida K. Catal. Commun. 2006, 68

Google Scholar
29 Hanson JR. Harpel S. Medina ICR. Rose D. J. Chem. Res., Synop. 1997, 432

Google Scholar
30 Narender N. Srinivasu P. Kulkarni SJ. Raghavan KV. Synth. Commun. 2000, 30: 3669

Google Scholar
31 Narender N. Krishna Mohan KVV. Vinod Reddy R. Srinivasu P. Kulkarni SJ. Raghavan KV. J. Mol. Catal. A: Chem. 2003, 192: 73

Google Scholar
32 Tajik H. Shirini F. Hassan-zadeh P. Rashtabadi HR. Synth. Commun. 2005, 35: 1947

Google Scholar
33 Narender N. Krishna Mohan KVV. Kulkarni SJ. J. Chem. Res., Synop. 2003, 597

Google Scholar
34 Kumar MA. Rohitha CN. Kulkarni SJ. Narender N. Synthesis 2010, 1629

Google Scholar
35 Krishna Mohan KVV. Narender N. Srinivasu P. Kulkarni SJ. Raghavan KV. Synth. Commun. 2004, 34: 2143

Google Scholar
36a Fanta PE. Synthesis 1974, 9

Google Scholar
36b Nilsson M. Tetrahedron Lett. 1966, 7: 679

Google Scholar
36c House HO. Respess WL. Whitesides GM. J. Org. Chem. 1966, 31: 3128

Google Scholar
36d Suzuki H. Abe H. Osuka A. Chem. Lett. 1980, 1363

Google Scholar
36e Matsui K. Tobita E. Ando M. Kondo K. Chem. Lett. 1981, 1719

Google Scholar
36f Suzuki H. Kobayashi T. Yoshida Y. Osuka A. Chem. Lett. 1983, 193

Google Scholar
37 Buttler AR. J. Chem. Educ. 1971, 36: 508 ; and references cited therein

Google Scholar
38 Orito K. Hatakeyama T. Takeo M. Suginome H. Synthesis 1995, 1273

Google Scholar
39 Yang SG. Kim YH. Tetrahedron Lett. 1999, 40: 6051

Google Scholar
40 Blackmore IJ. Boa AN. Murray EJ. Dennis M. Woodward S. Tetrahedron Lett. 1999, 40: 6671

Google Scholar
41 Olah GA. Wang Q. Sandford G. Prakash GKS. J. Org. Chem. 1993, 58: 3194

Google Scholar
42 Zupon M. Iskra J. Stavber S. Tetrahedron Lett. 1997, 38: 6305

Google Scholar
43 Carreno MC. Ruano JLG. Sanz G. Toledo MA. Urbano A. Tetrahedron Lett. 1996, 37: 4081

Google Scholar
44 Brunel Y. Rousseau G. Tetrahedron Lett. 1995, 36: 8217

Google Scholar
45 Hubig SM. Jung W. Kochi JK. J. Org. Chem. 1994, 59: 6233

Google Scholar
46 Barluenga J. Gonzalez JM. Garcia-Martin MA. Campos PJ. Ascnsio G. J. Org. Chem. 1993, 58: 2058

Google Scholar
47 Marko DM. Belyaev YA. Khim. Referat. Zhur. 1941, 4: 49

Google Scholar
48 Sy WW. Tetrahedron Lett. 1993, 34: 6223

Google Scholar
49 Bachki A. Foubelo F. Yus M. Tetrahedron 1994, 50: 5139

Google Scholar
50a Larock RC. Tetrahedron 1982, 38: 1713

Google Scholar
50b Burnett DA. Caplen MA. Domalski MS. Browne ME. Davis HR. Clader JW. Bioorg. Med. Chem. Lett. 2002, 12: 311

Google Scholar
50c Pomilio AB. Barolli MG. J. Labelled Compd. Radiopharm. 1997, 39: 927

Google Scholar
51 Iskra J. Stavber S. Zupan M. Synthesis 2004, 1869

Google Scholar
52 Narender N. Srinivasu P. Kulkarni SJ. Raghavan KV. Synth. Commun. 2002, 32: 2319

Google Scholar
53 Beinker P. Hanson JR. Meindl N. Medina ICR. J. Chem. Res., Synop. 1998, 204

Google Scholar
54a Dadswell HE. Kenner J. J. Chem. Soc. 1927, 1102

Google Scholar
54b De la Mare PB. Hassan M. J. Chem. Soc. 1958, 1519

Google Scholar
55 Reddy KSK. Narender N. Rohitha CN. Kulkarni SJ. Synth. Commun. 2008, 38: 3902

Google Scholar
56 Firouzabadi H. Iranpoor N. Kazemi S. Can. J. Chem. 2009, 87: 1675

Google Scholar
57 Narender N. Reddy KSK. Krishna Mohan KVV. Kulkarni SJ. Tetrahedron Lett. 2007, 48: 6124

Google Scholar
58 Krishna Mohan KVV. Narender N. Kulkarni SJ. Tetrahedron Lett. 2004, 45: 8015

Google Scholar

11

Ullmann’s Encyclopedia of Industrial Chemistry, 6th ed.; Wiley-VCH: Weinheim, 1998; electronic release.