Synthesis and Reactivity of Mixed Dimethylalkynylaluminum Reagents

Riccardo Piccardi; Serge Turcaud; Erica Benedetti; Laurent Micouin

doi:10.1055/s-0037-1610392

Synthesis, Table of Contents

CC BY ND NC 4.0 · Synthesis 2019; 51(01): 97-106
DOI: 10.1055/s-0037-1610392

short review

Copyright with the author

Synthesis and Reactivity of Mixed Dimethylalkynylaluminum Reagents

Riccardo Piccardi

,

Serge Turcaud

,

Erica Benedetti

,

Laurent Micouin *

Laboratoire de Chimie et Biochimie Pharmacologiques et Toxicologiques, UMR 8601 CNRS-Université Paris Descartes, Faculté des Sciences Fondamentales et Biomédicales, 45 rue des Saints-Pères, 75006 Paris, France Email: Laurent.micouin@parisdescartes.fr

› Author Affiliations

Abstract

All articles of this category

Published as part of the 50 Years SYNTHESIS – Golden Anniversary Issue

Abstract

Organoaluminum derivatives are mostly appreciated for their Lewis acidity properties, but generally not considered as reagents of choice in synthetic transformations involving the creation of C–C bonds. Among these species, dimethylalkynylaluminum reagents represent a special class of compounds, with, in many cases, unique reactivity. This review summarizes the preparation and reactivity of these organometallic reagents with a focus on their synthetic potential.

1 Introduction

2 Preparation of Dimethylalkynylaluminum Reagents

3 Reactivity of Dimethylalkynylaluminum Reagents

3.1 Reactions with Csp³ Electrophiles

3.2 Reactions with Csp² Electrophiles

4 Transition-Metal-Catalyzed Reactions

4.1 Addition to α,β-Unsaturated Enones

4.2 Coupling Reactions

5 Triple Bond Reactivity

6 Conclusion

Key words

organometallics - alkynes - organoaluminum reagents - alkynylation - metalation

Full Text

References

References
1 Hallwachs W, Schafarik A. Justus Liebigs Ann. Chem. 1859; 109: 207
2 Atwood DA, Yearwood BC. J. Organomet. Chem. 2000; 600: 186

3a Suzuki K, Nagasawa T, Saito S. e-EROS Encycl. Reagents Org. Synth. 2007;
3b The Chemistry of Organoaluminum Compounds . Micouin L, Marek I, Rappoport Z. Wiley; Chichester: 2017

4 Saito S. In Comprehensive Organometallic Chemistry III . Vol. 9. Mingos DM. P, Crabtree RH. Elsevier; Oxford: 2007: 245
5 Oishi M. In Science of Synthesis . Vol. 7. Yamamoto H. Thieme; Stuttgart: 2004: 261
6 Eisch JJ. In Comprehensive Organometallic Chemistry . Vol. 1. Wilkinson G, Stone FG. A, Abel EW. Pergamon; Oxford: 1982: 555
7 For a more general review on alkynylaluminum species see: Piccardi R, Micouin L, Jackowski O. In The Chemistry of Organoaluminum Compounds . Micouin L, Marek I, Rappoport Z. Wiley; Chichester: 2017: 157
8 Starowieyski KB, Chwojnowski A, Kusmierek Z. J. Organomet. Chem. 1980; 192: 147
9 Woo SH, Parker MH, Ploypradith P, Northrop J, Posner GH. Tetrahedron Lett. 1998; 39: 1533

10a Danishefsky S, Kitahara T, Tsai M, Dynak J. J. Org. Chem. 1976; 41: 1669
10b Verrier C, Carret S, Poisson J.-F. Org. Biomol. Chem. 2014; 12: 1875

11 Reinäcker R, Schwengers D. Justus Liebigs Ann. Chem. 1970; 737: 182
12 Binger P. Angew. Chem., Int. Ed. Engl. 1963; 2: 686
13 Feuvrie C, Blanchet J, Bonin M, Micouin L. Org. Lett. 2004; 6: 2333
14 Zhou Y, Lecourt T, Micouin L. Adv. Synth. Catal. 2009; 351: 2595
15 Kanbur U, Ellern A, Sadow AD. Organometallics
16 Piccardi R, Coffinet A, Benedetti E, Turcaud S, Micouin L. Synthesis 2016; 48: 3272

17a Zhu J, Quirion J.-C, Husson H.-P. Tetrahedron Lett. 1989; 30: 5137
17b Froelich O, Desos P, Bonin M, Quirion J.-C, Husson H.-P. J. Org. Chem. 1996; 61: 6700
17c Cutri S, Chiaroni A, Bonin M, Micouin L, Husson H.-P. J. Org. Chem. 2003; 68: 2645

18 Guerrier L, Royer J, Grierson DS, Husson H.-P. J. Am. Chem. Soc. 1983; 105: 7754
19 Ooi T, Uraguchi D, Kagoshima N, Maruoka K. Tetrahedron Lett. 1997; 38: 5679

20a Kessabi J, Beaudegnies R, Jung PM. J, Martin B, Montel F, Wendeborn S. Org. Lett. 2006; 8: 5629
20b Kessabi J, Beaudegnies R, Jung PM. J, Martin B, Montel F, Wendeborn S. Synthesis 2008; 655
20c Hamada N, Yoshida Y, Oishi S, Ohno H. Org. Lett. 2017; 19: 1875

21 Suga Y, Fuwa H, Sasaki M. J. Org. Chem. 2014; 79: 1656

22a Ley SV, Humphries AC, Eick H, Downham R, Ross AR, Boyce RJ, Pavey JB. J, Pietruszka J. J. Chem. Soc., Perkin Trans. 1 1998; 3907
22b Fuwa H, Sakamoto K, Muto T, Sasaki M. Tetrahedron 2015; 71: 6369

23 Korbad BL, Lee S.-H. Eur. J. Org. Chem. 2014; 5089
24 Shinoda M, Iseki K, Oguri T, Hayasi Y, Yamada S.-I, Shibasaki M. Tetrahedron Lett. 1986; 27: 87
25 Charoenying P, Davie DH, McKerrecher D, Taylor RJ. K. Tetrahedron Lett. 1996; 37: 1913
26 Bijoy P, Avery MA. Tetrahedron Lett. 1998; 39: 209
27 Ooi T, Kagoshima N, Maruoka K. J. Am. Chem. Soc. 1997; 119: 5754
28 Sasaki M, Tanino K, Miyashita M. J. Org. Chem. 2001; 66: 5388
29 Sasaki M, Hatta M, Tanino K, Miyashita M. Tetrahedron Lett. 2004; 45: 1911
30 Bournaud C, Bonin M, Micouin L. Org. Lett. 2006; 8: 3041
31 Bertolini F, Woodward S, Crott S, Pineschi M. Tetrahedron Lett. 2009; 50: 2515
32 Magnus P, Lacour J, Evans PE, Rigollier P, Tobler H. J. Am. Chem. Soc. 1998; 120: 12486

33a Lehmkuhl H, Ziegler K, Gellert H.-G. In Houben-Weyl . Thieme; Stuttgart: 1970. 4th ed, Vol. 13 158
33b Zweifel G, Miller JA. Org. React. 1984; 32: 375

34 Wang B, Bonin M, Micouin L. J. Org. Chem. 2005; 70: 6126
35 Korbad BL, Lee S.-H. Synlett 2013; 24: 1953
36 Trost BM, Biannic B. Org. Lett. 2015; 17: 1433
37 Jackowski O, Lecourt T, Micouin L. Org. Lett. 2011; 13: 5664
38 Pillard C, Desvergnes V, Py S. Tetrahedron Lett. 2007; 48: 1457
39 Bunlaksananusorn T, Lecourt T, Micouin L. Tetrahedron Lett. 2007; 48: 6209
40 Benamer M, Turcaud S, Royer J. Tetrahedron Lett. 2010; 51: 645
41 Turcaud S, Berhal F, Royer J. J. Org. Chem. 2007; 72: 7893
42 Kumar R, Turcaud S, Micouin L. Org. Lett. 2014; 16: 6192
43 Courant T, Kumar R, Turcaud S, Micouin L. Org. Lett. 2016; 18: 4818
44 Zhao T, Piccardi R, Micouin L. Org. Lett. 2018; 20: 5015
45 Gampe CM, Carreira EM. Chem. Eur. J. 2012; 18: 15761
46 Ahmar S, Fillion E. Org. Lett. 2014; 16: 5748

47a Carreño MC, González MP, Ribagorda M, Houk KN. J. Org. Chem. 1998; 63: 3687
47b Carreño MC, González MP, Ribagorda M, Fischer J. J. Org. Chem. 1996; 61: 6758

48 Hansen RT, Carr DB, Schwartz J. J. Am. Chem. Soc. 1978; 100: 2244

49a Larionov OV, Corey EJ. Org. Lett. 2010; 12: 300
49b Kwak Y.-S, Corey EJ. Org. Lett. 2004; 6: 3385

50 Wang B, Bonin M, Micouin L. Org. Lett. 2004; 6: 3481
51 Mo S, Shao X.-B, Zhang G, Li Q.-H. RSC Adv. 2017; 7: 27243
52 Paley RS, Snow SR. Tetrahedron Lett. 1990; 31: 5853
53 Yoshida T, Negishi E. J. Am. Chem. Soc. 1981; 103: 1276

54a Boardman LD, Bagheri V, Sawada H, Negishi E. J. Am. Chem. Soc. 1984; 106: 6105
54b Negishi E, Sawada H, Tour JM. J. Org. Chem. 1988; 53: 913

55 Zhou Y, Lecourt T, Micouin L. Angew. Chem. Int. Ed. 2010; 49: 2607