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Trotter, J.; Darby, W. In Organic Syntheses; Wiley: New York, 1955; Collect. Vol. III, p 460. We have optimized the workup and isolation conditions of this original report by replacing the use of hydrogen sulfide to decompose the copper salts with thioacetimide and isolating the final product 1 by chromatography instead of precipitation as a perchlorate salt. Preparations of 1 on a 0.5 mmol scale have been routinely carried out using these modifications. Details can be found in Supporting Information.
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Interestingly, despite the fact that the use of potassium tert-butoxide in ethanol should generate sodium ethoxide in situ, attempts to use a solution of sodium ethoxide in ethanol generated by the addition of sodium metal to ethanol have not led to satisfactory results.
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For reports of the Heck reaction in RTILs, see: Calo, V.; Nacci, A.; Lopez, L.; Napola, A. Tetrahedron Lett. 2001, 42, 4701. Battistuzzi, G.; Cacchi, S.; Fabrizi, G. Synlett 2002, 439. Calo, V.; Nacci, A.; Monopoli, A.; Lopez, L.; Cosmo, A. Tetrahedron 2001, 57, 6071. Boelm, V. P. W.; Herrmann, W. A. Chem. Eur. J. 2000, 6, 1017. Calo, V.; Nacci, A.; Lopez, L.; Mannarini, N. Tetrahedron Lett. 2000, 41, 8973. Herrmann, W. A.; Boehm, V. P. W. J. Organomet. Chem. 1999, 572, 141. Kaufmann, D. E.; Nouroozian, M.; Henze, H. Synlett 1996, 1091. Xu, L.; Chen, W.; Ross, J.; Xiao, J. Org. Lett. 2001, 3, 295. Okubo, K.; Shirai, M.; Yokoyama, C. Tetrahedron Lett. 2002, 43, 7115. See also ref 10.
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For reports of the Heck reaction in RTILs, see: Calo, V.; Nacci, A.; Lopez, L.; Napola, A. Tetrahedron Lett. 2001, 42, 4701. Battistuzzi, G.; Cacchi, S.; Fabrizi, G. Synlett 2002, 439. Calo, V.; Nacci, A.; Monopoli, A.; Lopez, L.; Cosmo, A. Tetrahedron 2001, 57, 6071. Boelm, V. P. W.; Herrmann, W. A. Chem. Eur. J. 2000, 6, 1017. Calo, V.; Nacci, A.; Lopez, L.; Mannarini, N. Tetrahedron Lett. 2000, 41, 8973. Herrmann, W. A.; Boehm, V. P. W. J. Organomet. Chem. 1999, 572, 141. Kaufmann, D. E.; Nouroozian, M.; Henze, H. Synlett 1996, 1091. Xu, L.; Chen, W.; Ross, J.; Xiao, J. Org. Lett. 2001, 3, 295. Okubo, K.; Shirai, M.; Yokoyama, C. Tetrahedron Lett. 2002, 43, 7115. See also ref 10.
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For reports of the Heck reaction in RTILs, see: Calo, V.; Nacci, A.; Lopez, L.; Napola, A. Tetrahedron Lett. 2001, 42, 4701. Battistuzzi, G.; Cacchi, S.; Fabrizi, G. Synlett 2002, 439. Calo, V.; Nacci, A.; Monopoli, A.; Lopez, L.; Cosmo, A. Tetrahedron 2001, 57, 6071. Boelm, V. P. W.; Herrmann, W. A. Chem. Eur. J. 2000, 6, 1017. Calo, V.; Nacci, A.; Lopez, L.; Mannarini, N. Tetrahedron Lett. 2000, 41, 8973. Herrmann, W. A.; Boehm, V. P. W. J. Organomet. Chem. 1999, 572, 141. Kaufmann, D. E.; Nouroozian, M.; Henze, H. Synlett 1996, 1091. Xu, L.; Chen, W.; Ross, J.; Xiao, J. Org. Lett. 2001, 3, 295. Okubo, K.; Shirai, M.; Yokoyama, C. Tetrahedron Lett. 2002, 43, 7115. See also ref 10.
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For reports of the Heck reaction in RTILs, see: Calo, V.; Nacci, A.; Lopez, L.; Napola, A. Tetrahedron Lett. 2001, 42, 4701. Battistuzzi, G.; Cacchi, S.; Fabrizi, G. Synlett 2002, 439. Calo, V.; Nacci, A.; Monopoli, A.; Lopez, L.; Cosmo, A. Tetrahedron 2001, 57, 6071. Boelm, V. P. W.; Herrmann, W. A. Chem. Eur. J. 2000, 6, 1017. Calo, V.; Nacci, A.; Lopez, L.; Mannarini, N. Tetrahedron Lett. 2000, 41, 8973. Herrmann, W. A.; Boehm, V. P. W. J. Organomet. Chem. 1999, 572, 141. Kaufmann, D. E.; Nouroozian, M.; Henze, H. Synlett 1996, 1091. Xu, L.; Chen, W.; Ross, J.; Xiao, J. Org. Lett. 2001, 3, 295. Okubo, K.; Shirai, M.; Yokoyama, C. Tetrahedron Lett. 2002, 43, 7115. See also ref 10.
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For reports of the Heck reaction in RTILs, see: Calo, V.; Nacci, A.; Lopez, L.; Napola, A. Tetrahedron Lett. 2001, 42, 4701. Battistuzzi, G.; Cacchi, S.; Fabrizi, G. Synlett 2002, 439. Calo, V.; Nacci, A.; Monopoli, A.; Lopez, L.; Cosmo, A. Tetrahedron 2001, 57, 6071. Boelm, V. P. W.; Herrmann, W. A. Chem. Eur. J. 2000, 6, 1017. Calo, V.; Nacci, A.; Lopez, L.; Mannarini, N. Tetrahedron Lett. 2000, 41, 8973. Herrmann, W. A.; Boehm, V. P. W. J. Organomet. Chem. 1999, 572, 141. Kaufmann, D. E.; Nouroozian, M.; Henze, H. Synlett 1996, 1091. Xu, L.; Chen, W.; Ross, J.; Xiao, J. Org. Lett. 2001, 3, 295. Okubo, K.; Shirai, M.; Yokoyama, C. Tetrahedron Lett. 2002, 43, 7115. See also ref 10.
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For reports of the Heck reaction in RTILs, see: Calo, V.; Nacci, A.; Lopez, L.; Napola, A. Tetrahedron Lett. 2001, 42, 4701. Battistuzzi, G.; Cacchi, S.; Fabrizi, G. Synlett 2002, 439. Calo, V.; Nacci, A.; Monopoli, A.; Lopez, L.; Cosmo, A. Tetrahedron 2001, 57, 6071. Boelm, V. P. W.; Herrmann, W. A. Chem. Eur. J. 2000, 6, 1017. Calo, V.; Nacci, A.; Lopez, L.; Mannarini, N. Tetrahedron Lett. 2000, 41, 8973. Herrmann, W. A.; Boehm, V. P. W. J. Organomet. Chem. 1999, 572, 141. Kaufmann, D. E.; Nouroozian, M.; Henze, H. Synlett 1996, 1091. Xu, L.; Chen, W.; Ross, J.; Xiao, J. Org. Lett. 2001, 3, 295. Okubo, K.; Shirai, M.; Yokoyama, C. Tetrahedron Lett. 2002, 43, 7115. See also ref 10.
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