Solid Organozinc Pivalates: A New Class of Zinc Organometallics with Greatly Enhanced Air- and Moisture-Stability

Yi-Hung Chen; Mario Ellwart; Vladimir Malakhov; Paul Knochel

doi:10.1055/s-0036-1588843

Synthesis, Inhaltsverzeichnis

Synthesis 2017; 49(15): 3215-3223
DOI: 10.1055/s-0036-1588843

short review

Solid Organozinc Pivalates: A New Class of Zinc Organometallics with Greatly Enhanced Air- and Moisture-Stability

Yi-Hung Chen

Ludwig-Maximilians-Universität, Department Chemie und Biochemie, Butenandtstr. 5-13, 81377 München, Germany eMail: paul.knochel@cup.uni-muenchen.de

,

Mario Ellwart

Ludwig-Maximilians-Universität, Department Chemie und Biochemie, Butenandtstr. 5-13, 81377 München, Germany eMail: paul.knochel@cup.uni-muenchen.de

,

Vladimir Malakhov

Ludwig-Maximilians-Universität, Department Chemie und Biochemie, Butenandtstr. 5-13, 81377 München, Germany eMail: paul.knochel@cup.uni-muenchen.de

,

Paul Knochel *

Ludwig-Maximilians-Universität, Department Chemie und Biochemie, Butenandtstr. 5-13, 81377 München, Germany eMail: paul.knochel@cup.uni-muenchen.de

› Institutsangaben

Abstract

Alle Artikel dieser Rubrik

Dedicated to Prof. Herbert Mayr on the occasion of his 70^th birthday

Abstract

Organozinc species are powerful reagents for performing carbon–carbon and carbon–heteroatom bond-forming reactions in the presence of a transition-metal catalyst. However, extended applications of zinc reagents have been hampered by their moderate air- and moisture-stability. This short review presents our recent developments on the preparation of solid aryl, benzyl, heteroaryl, allyl zinc pivalates and zinc amide enolate reagents with greatly enhanced stability toward to air and moisture.

1 Introduction

2 Preparation of Organozinc Pivalates

2.1 Using Organic Halides as Substrates

2.2 Using a Directed Metalation on Functionalized Arenes and Heteroarenes

2.3 Preparation of Solid Allylic Zinc Pivalates

3 General Reactivity Patterns of Organozinc Pivalates

3.1 General Aspects

3.2 Transition-Metal-Catalyzed Cross-Couplings

3.3 Other Carbon–Carbon Bond-Forming Reactions Using Organozinc Pivalates

3.4 Preparation and Reactions of Solid, Salt-Stabilized Zinc Amide Enolates as New, Convenient Reformatsky Reagents

4 Conclusion

Key words

zinc - magnesium - cross-coupling - transition metal - metalation

Volltext

Referenzen

References
1 Frankland E. Justus Liebigs Ann. Chem. 1849; 71: 171
2 Frankland E. J. Chem. Soc. 1850; 263
3 Diethylzinc was classified as extremely flammable, corrosive and dangerous for the environment by Dangerous Substances Directive. Regulations (EC) No 1271/2008 of the European Parliament and of the Council. Official J. Eur. Union 2008, 1-1355.

4a Hupe E. Knochel P. Org. Lett. 2001; 3: 127
4b Boudier A. Hupe E. Knochel P. Angew. Chem. Int. Ed. 2000; 39: 2294

5 Knochel P. In Science of Synthesis: Houben-Weyl Methods of Molecular Transformations. Vol. 3. O’Neil IA. Thieme; Stuttgart: 2004: 5-90

6a Knochel P. Millot N. Rodriguez AL. Tucker CE. In Preparation and Applications of Functionalized Organozinc Compounds. Organic Reactions . Vol. 58. Wiley-VCH; Weinheim: 2004: 417-759
6b Dilman AD. Levin VV. Tetrahedron Lett. 2016; 57: 3986
6c Knochel P. Leuser H. Cong L.-Z. Perrone S. Kneisel FF. In Handbook of Functionalized Organometallics . Wiley-VCH; Weinheim: 2008: 251

7a Negishi E.-i. Acc. Chem. Res. 1982; 15: 340
7b Negishi E.-i. Angew. Chem. Int. Ed. 2011; 50: 6738

8a Dagousset G. Francois C. Leon T. Blanc R. Sansiaume-Dagousset E. Knochel P. Synthesis 2014; 46: 3133
8b Metal-Catalyzed Cross-Coupling Reactions and More . Vol. 1. de Meijere A. Bräse S. Oestreich M. Wiley-VCH; Weinheim: 2014: 133-278
8c Benischke AD. Ellwart M. Becker MR. Knochel P. Synthesis 2016; 48: 1101

9 O’Donovan MR. Mee CD. Fenner S. Teasdale A. Phillips DH. Mutat. Res. 2011; 724: 1

10a Boersma J. Noltes JG. J. Organomet. Chem. 1968; 13: 291
10b Boersma J. Verbeek F. Noltes JG. J. Organomet. Chem. 1971; 33: C53

11 Charette AB. Molinaro C. Brochu C. J. Am. Chem. Soc. 2001; 123: 12160
12 Manolikakes SM. Ellwart M. Stathakis CI. Knochel P. Chem. Eur. J. 2014; 20: 12289
13 Bernhardt S. Manolikakes G. Kunz T. Knochel P. Angew. Chem. Int. Ed. 2011; 50: 9205
14 Piller FM. Metzger A. Schade MA. Haag BA. Gavryushin A. Knochel P. Chem. Eur. J. 2009; 15: 7192

15a Krasovskiy A. Knochel P. Angew. Chem. Int. Ed. 2004; 43: 3333
15b Klatt T. Markiewicz JT. Saemann C. Knochel P. J. Org. Chem. 2014; 79: 4253

16 Hernán-Gómez A. Herd E. Hevia E. Kennedy AR. Knochel P. Koszinowski K. Manolikakes SM. Mulvey RE. Schnegelsberg C. Angew. Chem. Int. Ed. 2014; 53: 2706

17a Anctil EJ.-G. Snieckus V. J. Organomet. Chem. 2002; 653: 150
17b Mulvey RE. Mongin F. Uchiyama M. Kondo Y. Angew. Chem. Int. Ed. 2007; 46: 3802
17c Haag B. Mosrin M. Ila H. Malakhov V. Knochel P. Angew. Chem. Int. Ed. 2011; 50: 9794
17d Snieckus V. Anctil EJ.-G. In Metal-Catalyzed Cross-Coupling Reactions and More . Vol. 3. de Meijere A. Brase S. Oestreich M. Wiley-VCH; Weinheim: 2014: 1067-1133

18 Stathakis CI. Bernhardt S. Quint V. Knochel P. Angew. Chem. Int. Ed. 2012; 51: 9428
19 Krasovskiy A. Krasovskaya V. Knochel P. Angew. Chem. Int. Ed. 2006; 45: 2958
20 Stathakis CI. Manolikakes SM. Knochel P. Org. Lett. 2013; 15: 1302

21a Mosrin M. Knochel P. Org. Lett. 2009; 11: 1837
21b Mosrin M. Monzon G. Bresser T. Knochel P. Chem. Commun. 2009; 5615
21c Bresser T. Mosrin M. Monzon G. Knochel P. J. Org. Chem. 2010; 75: 4686

22a Bresser T. Knochel P. Angew. Chem. Int. Ed. 2011; 50: 1914
22b Duez S. Steib AK. Manolikakes SM. Knochel P. Angew. Chem. Int. Ed. 2011; 50: 7686

23 Colombe JR. Bernhardt S. Stathakis C. Buchwald SL. Knochel P. Org. Lett. 2013; 15: 5754

24a Courtois G. Al-Arnaout A. Miginiac L. Tetrahedron Lett. 1985; 26: 1027
24b Villieras J. Rambaud M. Synthesis 1982; 924
24c Dembele YA. Belaud C. Hitchcock P. Villieras J. Tetrahedron: Asymmetry 1992; 3: 351
24d Nyzam V. Belaud C. Zammattio F. Villieras J. Tetrahedron: Asymmetry 1996; 7: 1835

25a Ren H. Dunet G. Mayer P. Knochel P. J. Am. Chem. Soc. 2007; 129: 5376
25b Helm MD. Mayer P. Knochel P. Chem. Commun. 2008; 1916
25c Saemann C. Knochel P. Synthesis 2013; 45: 1870

26 Ellwart M. Knochel P. Angew. Chem. Int. Ed. 2015; 54: 10662
27 Metal-Catalyzed Cross-Coupling Reactions and More . de Meijere A. Brase S. Oestreich M. Wiley-VCH; Weinheim: 2014: 1576
28 Farina V. Krishnan B. J. Am. Chem. Soc. 1991; 113: 9585
29 Hayashi T. Konishi M. Kobori Y. Kumada M. Higuchi T. Hirotsu K. J. Am. Chem. Soc. 1984; 106: 158
30 Guram AS. Buchwald SL. J. Am. Chem. Soc. 1994; 116: 7901

31a Hadei N. Kantchev EA. B. O’Brien CJ. Organ MG. Org. Lett. 2005; 7: 3805
31b McCann LC. Hunter HN. Clyburne JA. C. Organ MG. Angew. Chem. Int. Ed. 2012; 51: 7024

32 Seechurn CC. C. J. Kitching MO. Colacot TJ. Snieckus V. Angew. Chem. Int. Ed. 2012; 51: 5062

33a Suzuki A. Pure Appl. Chem. 1991; 63: 419
33b Miyaura N. Suzuki A. Chem. Rev. 1995; 95: 2457
33c Suzuki A. J. Organomet. Chem. 1999; 576: 147

34 Negishi E.-i. King AO. Okukado N. J. Org. Chem. 1977; 42: 1821

35a Knappkea CE. I. von Wangelin AJ. Chem. Soc. Rev. 2011; 40: 4948
35b Corriu RJ. P. Masse J. P. J. Chem. Soc., Chem. Commun. 1972; 144
35c Tamao K. Sumitani K. Kumada M. J. Am. Chem. Soc. 1972; 94: 4374

36 Hatanaka Y. Hiyama T. J. Org. Chem. 1988; 53: 918

37a Denmark SE. Regens CS. Acc. Chem. Res. 2008; 41: 1486
37b Denmark SE. Yang S.-M. J. Am. Chem. Soc. 2002; 124: 2102

38 Huang X. Anderson KW. Zim D. Jiang L. Klapars A. Buchwald SL. J. Am. Chem. Soc. 2003; 125: 6653

39a Gosmini C. Begouin J.-M. Moncomble A. Chem. Commun. 2008; 3221
39b Cahiez G. Moyeux A. Chem. Rev. 2010; 110: 1435
39c Gosmini C. Moncomble A. Isr. J. Chem. 2010; 50: 568

40a Hammann JM. Steib AK. Knochel P. Org. Lett. 2014; 16: 6500
40b Hammann JM. Haas D. Knochel P. Angew. Chem. Int. Ed. 2015; 54: 4478
40c Hofmayer MS. Hammann JM. Haas D. Knochel P. Org. Lett. 2016; 18: 6456
40d Hammann JM. Haas D. Tüllmann C.-P. Karaghiosoff K. Knochel P. Org. Lett. 2016; 18: 4778

41 Haas D. Hammann JM. Lutter FH. Knochel P. Angew. Chem. Int. Ed. 2016; 55: 3809
42 Hammann JM. Lutter FH. Haas D. Knochel P. Angew. Chem. Int. Ed. 2017; 56: 1082

43a Knochel P. Yeh MC. P. Berk SC. Talbert J. J. Org. Chem. 1988; 53: 2390
43b Knochel P. Perea JJ. A. Jones P. Tetrahedron 1998; 54: 8275
43c Boudier A. Bromm LO. Lotz M. Knochel P. Angew. Chem. Int. Ed. 2000; 39: 4414
43d Knochel P. Millot N. Rodriguez AL. Tucker CE. Org. React. 2001; 58: 417

44 Normant JF. Alexakis A. Synthesis 1981; 841
45 Shannon J. Bernier D. Rawson D. Woodward S. Chem. Commun. 2007; 3945
46 Le Notre J. Allen JC. Frost CG. Chem. Commun. 2008; 3795

47a Takaya Y. Ogasawara M. Hayashi T. Sakai M. Miyaura N. J. Am. Chem. Soc. 1998; 120: 5579
47b Hayashi T. Bull. Chem. Soc. Jpn. 2004; 77: 13

48a Cozzi PG. Angew. Chem. Int. Ed. 2007; 46: 2568
48b Haraguchi R. Matsubara S. Synthesis 2014; 46: 2272

49 Chen Y.-H. Ellwart M. Toupalas G. Ebe Y. Knochel P. Angew. Chem. Int. Ed. 2017; 56: 4612
50 Velezheva VS. Kornienko AG. Topilin SV. Turashev AD. Peregudov AS. Brennan PJ. J. Heterocycl. Chem. 2006; 43: 873