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
Synthesis 2020; 52(22): 3446-3451
DOI: 10.1055/s-0040-1707219
DOI: 10.1055/s-0040-1707219
paper
Neodymium-Promoted Highly Selective Carbon–Carbon Double Bond Formation of Ketones with Allyl Halides in the Presence of Diethyl Phosphite
We gratefully acknowledge the project funded by the Priority Academic Program Development of Jiangsu Higher Education Institutions and the National Natural Science Foundation of China (No. 21072143) for financial support.Further Information
Publication History
Received: 25 April 2020
Accepted after revision: 27 June 2020
Publication Date:
12 August 2020 (online)
Abstract
The carbon–carbon double bond formation via neodymium-mediated Barbier-type reaction of ketones and allyl halides in the presence of diethyl phosphite is reported for the first time. The reaction is highly α-regioselective and was conveniently carried out under mild conditions in a one-pot fashion. From a synthetic point of view, a series of conjugated alkenes were obtained in moderate to good yields in this one-pot reaction with feasible reaction conditions.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0040-1707219.
- Supporting Information
-
References
- 1a Girard P, Namy JL, Kagan HB. Nouv. J. Chim. 1977; 1: 5
- 1b Girard P, Namy JL, Kagan HB. J. Am. Chem. Soc. 1980; 102: 2693
- 2a Edmonds DJ, Johnston D, Procter DJ. Chem. Rev. 2004; 104: 3371
- 2b Procter DJ, Flowers RA. II, Skrydstrup T. Organic Synthesis Using Samarium Diiodide: A Practical Guide . Cambridge; Royal Society of Chemistry: 2010
- 2c Molander GA. Acc. Chem. Res. 1998; 31: 603
- 2d Kagan HB. Tetrahedron 2003; 59: 10351
- 2e Gopalaiah K, Kagan HB. New J. Chem. 2008; 32: 607
- 2f Szostak M, Fazakerley NJ, Parmar D, Procter DJ. Chem. Rev. 2014; 114: 5959
- 2g Molander GA, Harris CR. Tetrahedron 1998; 54: 3321
- 2h Hasegawa E, Curran DP. Tetrahedron Lett. 1993; 34: 1717
- 2i Sturino CF, Fallis AG. J. Am. Chem. Soc. 1994; 116: 7447
- 2j Bartulovich CO, Flowers RA. II. Dalton Trans. 2019; 48: 16142
- 2k Flowers RA. II. Synlett 2008; 1427
- 3a Evans WJ, Workman PS, Allen NT. Org. Lett. 2003; 5: 2041
- 3b Makarenko NP, Kurskii YA, Evans WJ, Bochkarev MN. Polyhedron 2006; 25: 1105
- 3c Burin ME, Smirnova MV, Fukin GK, Baranov EV, Bochkarev MN. Eur. J. Inorg. Chem. 2006; 351
- 3d Fagin AA, Balashova TV, Kusyaev DM, Kulikova TI, Glukhova TA, Jaroschik F, Momin A, Nief F, Le Goff XF, Deacon GB, Junk PC. Angew. Chem. Int. Ed. 2009; 48: 1117
- 4a Bochkarev MN, Fedushkin IL, Fagin AA, Petrovskaya TV, Ziller JW, Broomhall-Dillard RN, Evans WJ. Angew. Chem., Int. Ed. Engl. 1997; 36: 133
- 4b Evans WJ, Allen NT. J. Am. Chem. Soc. 2000; 122: 2118
- 4c Turcitu D, Nief F, Ricard L. Chem. Eur. J. 2003; 9: 4916
- 5a Bochkarev MN, Fagin AA. Chem. Eur. J. 1999; 5: 2990
- 5b Evans WJ, Allen NT, Ziller JW. J. Am. Chem. Soc. 2000; 122: 11749
- 5c Xiang X, Shen QS, Wang JL, Zhu ZY, Huang W, Zhou XG. Organometallics 2008; 27: 1959
- 6a Basu MK, Banik BK. Tetrahedron Lett. 2001; 42: 187
- 6b Miller RS, Sealy JM, Shabangi M, Kuhlman ML, Fuchs JR, Flowers RA. II. J. Am. Chem. Soc. 2000; 122: 7718
- 6c Asano Y, Suzuki S, Aoyama T, Shimizu K, Kajitani M, Yokoyama Y. Synthesis 2007; 1309
- 6d Zörb A, Brückner R. Eur. J. Org. Chem. 2010; 4785
- 6e Ready J, Reisman MS. E, Hirata M, Weiss MM, Tamaki K, Ovaska TV, Wood JL. Angew. Chem. Int. Ed. 2004; 43: 1270
- 6f Reisman SE, Ready JM, Hasuoka A, Smith CJ, Wood JL. J. Am. Chem. Soc. 2006; 128: 1448
- 6g Reisman SE, Ready JM, Weiss MM, Hasuoka A, Hirata M, Tamaki K, Ovaska TV, Smith CJ, Wood JL. J. Am. Chem. Soc. 2008; 130: 2087
- 6h Matsukawa S, Hinakubo Y. Org. Lett. 2003; 5: 1221
- 6i Guazzelli G, Grazia SD, Collins KD, Matsubara H, Spain M, Procter DJ. J. Am. Chem. Soc. 2009; 131: 7214
- 6j Szostak M, Spain M, Procter DJ. Nat. Protoc. 2012; 7: 970
- 6k Duffy LA, Matsubara H, Procter DJ. J. Am. Chem. Soc. 2008; 130: 1136
- 7a Dolgoplosk BA, Tinyakova EI, Markevich IN, Soboleva TV, Chernenko GM, Sharaev OK, Yakovlev VA. J. Organomet. Chem. 1983; 255: 71
- 7b Schumann H, Mueller J, Bruncks N, Lauke H, Pickardt J, Schwarz H, Eckart K. Organometallics 1984; 3: 69
- 7c Yokoo K, Fujiwara Y, Fukagawa T, Taniguchi H. Polyhedron 1983; 2: 1101
- 7d Kawabata H, Nishino T, Nishiyama Y, Sonoda N. Tetrahedron Lett. 2002; 43: 4911
- 7e Hou ZM, Fujiwara Y, Jintoku T, Mine N, Yokoo K, Taniguchi H. J. Org. Chem. 1987; 52: 3524
- 8a Yanada R, Bessho K, Yanada K. Chem. Lett. 1994; 1279
- 8b Akane N, Hatano T, Kusui H, Nishiyama Y, Ishii Y. J. Org. Chem. 1994; 59: 7902
- 8c Yanada R, Bessho K, Yanada K. Synlett 1995; 1261
- 8d Yanada R, Negoro N, Yanada K, Fujita T. Tetrahedron Lett. 1996; 37: 9313
- 8e Yanada R, Negoro N, Yanada K, Fujita T. Tetrahedron Lett. 1997; 38: 3271
- 8f Wang L, Zhang Y. Tetrahedron 1998; 54: 11129
- 9a Zhu ZY, Wang JL, Zhang ZX, Xiang X, Zhou XG. Organometallics. 2007; 26: 2499
- 9b Chen WF, Li KB, Hu ZQ, Wang LL, Lai GQ, Li ZF. Organometallics 2011; 30: 2026
- 10a Hou ZM, Fujiwara Y, Jintoku T, Mine N, Yokoo K, Taniguchi H. J. Org. Chem. 1987; 52: 3524
- 10b Imamoto T, Kusumoto T, Hatanaka Y, Yokoyama M. Tetrahedron Lett. 1982; 23: 1353
- 10c Fukuzawa S, Fujinami T, Sakai S. J. Chem. Soc., Chem. Commun. 1986; 475
- 10d Fukuzawa S, Sumimoto N, Fujinami T, Sakai S. J. Org. Chem. 1990; 55: 1328
- 11a Hou Z, Fujiwara Y, Taniguchi H. J. Org. Chem. 1988; 53: 3118
- 11b Hou Z, Taniguchi H, Fujiwara Y. Chem. Lett. 1987; 305
- 11c Takaki K, Tsubaki Y, Tanaka S, Beppu F, Fujiwara Y. Chem. Lett. 1990; 203
- 11d Takaki K, Beppu F, Tanaka S, Jintoku T, Fujiwara Y. J. Chem. Soc., Chem. Commun. 1990; 516
- 11e Takaki K, Nagase K, Beppu F, Fujiwara Y. Chem. Lett. 1991; 1665
- 12a Nishino T, Nishiyama Y, Sonoda N. Heteroat. Chem. 2000; 11: 81
- 12b Nishino T, Nishiyama Y, Sonoda N. Heteroat. Chem. 2002; 13: 131
- 12c Nishino T, Watanabe T, Okada M, Nishiyama Y, Sonoda N. J. Org. Chem. 2002; 67: 966
- 12d Nishino T, Nishiyama Y, Sonoda N. Tetrahedron Lett. 2002; 43: 3689
- 13 Wu S, Li Y, Zhang S. J. Org. Chem. 2016; 81: 8070
- 14 Zhang F, Wang R, Wu S, Wang P, Zhang S. RSC Adv. 2016; 6: 87710
- 15a Nicolaou KC, Ramphal JY, Petasis NA, Serhan CN. Angew. Chem. Int. Ed. 1991; 30: 1100
- 15b Sandri J, Viala J. J. Org. Chem. 1995; 60: 6627
- 15c Lucet D, Gall TL, Mioskowski C. Angew. Chem. Int. Ed. 1998; 37: 2580
- 15d Kotti SR. S. S, Timmons C, Li G.-G. Chem. Biol. Drug Des. 2006; 67: 101
- 15e Takao K, Munakata R, Tadano K. Chem. Rev. 2005; 105: 4779
- 15f Alvarez R, Vaz B, Gronemeyer H, de Lera AR. Chem. Rev. 2014; 114: 1
- 16a Boutagy J, Thomas R. Chem. Rev. 1974; 74: 87
- 16b Maryanoff BE, Reitz AB. Chem. Rev. 1989; 89: 863
- 17a Chan TH. Acc. Chem. Res. 1977; 10: 442
- 17b Ager DJ. Synthesis 1984; 384
- 17c Ager DJ. Org. React. 1990; 38: 1
- 17d Julia M, Paris J.-H. Tetrahedron Lett. 1973; 4833
- 18a Shoemaker BH, Boord CE. J. Am. Chem. Soc. 1931; 53: 1505
- 18b Schniepp LE, Geller HH. J. Am. Chem. Soc. 1945; 67: 54
- 18c Cope AC, Bumgardner CL. J. Am. Chem. Soc. 1957; 79: 960
- 18d Curry MJ, Stevens ID. R. J. Chem. Soc., Perkin Trans. 1 1980; 1756
- 18e Shibata K, Mitsunobu O. Bull. Chem. Soc. Jpn. 1992; 65: 3163
- 18f Yadav JS, Reddy BV. S, Reddy PM. K, Gupta MK. Tetrahedron Lett. 2005; 46: 8411
- 18g Lee PH, Heo Y, Seomoon D, Kim S, Lee K. Chem. Commun. 2005; 1874
- 19a Hernandez D, Larson GL. J. Org. Chem. 1984; 49: 4285
- 19b Lee K, Lee J, Lee PH. J. Org. Chem. 2002; 67: 8265
- 19c Caló V, Fiandanese V, Nacci A, Scilimati A. Tetrahedron Lett. 1995; 36: 171
- 19d Hirotada K, Hiroshi S, Koichiro O. Tetrahedron 2001; 57: 10063
- 19e Baker-Glenn CA. G, Barrett AG. M, Gray AA, Procopiou PA, Ruston M. Tetrahedron Lett. 2005; 46: 7427
- 20a Li Y, Hu Y.-Y, Zhang S.-L. Chem. Commun. 2013; 49: 10635
- 20b Hu Y.-Y, Zhao T, Zhang S.-L. Chem. Eur. J. 2010; 16: 1697
- 21a Wang T.-Q, Hu Y.-Y, Zhang S.-L. Org. Biomol. Chem. 2010; 8: 2312
- 21b Qi W.-K, Wang P.-P, Fan L.-Y, Zhang S.-L. J. Org. Chem. 2013; 78: 5918
- 22 Cui H, Li Y, Zhang S.-L. Org. Biomol. Chem. 2012; 10: 2862
For selected examples, see: