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CC BY-ND-NC 4.0 · Synthesis 2019; 51(01): 97-106
DOI: 10.1055/s-0037-1610392
DOI: 10.1055/s-0037-1610392
short review
Synthesis and Reactivity of Mixed Dimethylalkynylaluminum Reagents
A part of the work reported in this review and conducted in our lab has been finance by ANR (TRIBAL and AluMeth grants)Further Information
Publication History
Received: 20 October 2018
Accepted: 29 October 2018
Publication Date:
20 November 2018 (online)
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
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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; DOI: 10.1002/9780470842898.rt216.pub2.
- 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 DOI: 10.1021/acs.organomet.8b00374.
- 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