Halodiazirines as Valuable Reagents for the Synthesis of Halocyclo­propanes

This short review is dedicated to Prof. Alain Krief on the occasion of his 80^th birthday.

Abstract

Halodiazirines have emerged as very useful reagents in photochemically or thermally mediated cyclopropanation reactions with alkenes. This short review highlights the synthetic applications of these reagents as precursors of halocarbenes in transformations with various alkenes.

1 Introduction

2 Cyclopropanation of Aryl Halodiazirines

3 Tandem Reactions Using Aryl Halodiazirines

4 Cyclopropanation of Alkyl- and Benzyl-halodiazirines

5 Cyclopropanation of Other Halodiazirines

6 Reactions of Halodiazirines with Alkynes

7 Conclusion and Outlook

Key words

diazirines - carbenes - cycloaddition - cyclopropanes - photochemistry

• References

• 1 Moss RA. Acc. Chem. Res. 2006; 39: 267
• 2 Moss RA, Tian J, Chu G, Sauers RR, Krogh-Jespersen K. Pure Appl. Chem. 2007; 79: 993
• 3 Creary X. Acc. Chem. Res. 1992; 25: 31
• 4 Graham WH. J. Am. Chem. Soc. 1965; 87: 4396
• 5 Martinu T, Dailey WP. J. Org. Chem. 2006; 71: 5012
• 6 Martinu T, Dailey WP. J. Org. Chem. 2004; 69: 7359
• 7 Martinu T, Boehm S, Hanzlova E. Eur. J. Org. Chem. 2011; 6254
• 8 Padwa A, Pulwer MJ, Blacklock TJ. Org. Synth. 1981; 60: 53
• 9 Schmitz E, Sonnenschein H, Kuban RJ. Tetrahedron Lett. 1985; 26: 4911
• 10 Doyle MP, Terpstra JW, Winter CH. Tetrahedron Lett. 1984; 25: 901
• 11 Bertram AK, Liu MT. H. J. Chem. Soc., Chem. Commun. 1993; 467
• 12 Bonneau R, Grobys M, Liu MT. H, Himori M, Fukushima K, Ibata T. Res. Chem. Intermed. 1994; 20: 141
• 13 Komatsu K, Kagayama A, Murata Y, Sugita N, Kobayashi K, Nagase S, Wan TS. M. Chem. Lett. 1993; 2163
• 14 Kooistra FB, Leuning TM, Maroto Martinez E, Hummelen JC. Chem. Commun. 2010; 46: 2097
• 15 Liu MT. H, Choe Y.-K, Kimura M, Kobayashi K, Nagase S, Wakahara T, Niino Y, Ishitsuka MO, Maeda Y, Akasaka T. J. Org. Chem. 2003; 68: 7471
• 16 Moss RA, Lu Z, Sauers RR. Tetrahedron Lett. 2010; 51: 5940
• 17 Doyle MP, Loh KL, Nishioka LI, McVickar MB, Liu MT. H. Tetrahedron Lett. 1986; 27: 4395
• 18 Soundararajan N, Platz MS, Jackson JE, Doyle MP, Oon SM, Liu MT. H, Anand SM. J. Am. Chem. Soc. 1988; 110: 7143
• 19 Moss RA, Lawrynowicz W. J. Org. Chem. 1984; 49: 3828
• 20 Cox DP, Moss RA, Terpinski J. J. Am. Chem. Soc. 1983; 105: 6513
• 21 Moss RA, Shen Y.-M, Wang L, Krogh-Jespersen K. Org. Lett. 2011; 13: 4752
• 22 Wang L, Krogh-Jespersen K, Moss RA. J. Org. Chem. 2015; 80: 7590
• 23 Rigby JH, Aasmul M. Heterocycles 2004; 62: 143
• 24 Schmitz E, Sonnenschein H. Z. Chem. 1987; 27: 171
• 25 Sonnenschein H, Schmitz E, Pritzkow W. Liebigs Ann. Chem. 1990; 277
• 26 Li C, Vasella A. Helv. Chim. Acta 1993; 76: 197
• 27 Dherange BD, Kelly PQ, Liles JP, Sigman MS, Levin MD. J. Am. Chem. Soc. 2021; 143: 11337
• 28 Moss RA, Mamantov A. J. Am. Chem. Soc. 1970; 92: 6951
• 29 Tomioka H, Hayashi N, Izawa Y, Liu MT. H. J. Chem. Soc., Chem. Commun. 1984; 476
• 30 Liu MT. H, Bonneau R. J. Org. Chem. 1992; 57: 2483
• 31 Moss RA, Perez LA, Wlostowska J, Guo W, Krogh-Jespersen K. J. Org. Chem. 1982; 47: 4177
• 32 Mitsch RA, Neuvar EW, Koshar RJ, Dybvig DH. J. Heterocycl. Chem. 1965; 2: 371
• 33 Padwa A, Eastman D. J. Org. Chem. 1969; 34: 2728
• 34 Komatsu K, Arai M, Hattori Y, Fukuyama K, Katsube Y, Okamoto K. J. Org. Chem. 1987; 52: 2183