Electrochemically Driven Catalytic Pd(0)/Cr(II) Mediated Coupling of Organic Halides with Aldehydes. The Nozaki-Hiyama-Kishi Reaction.
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Published:1997-09
Issue:35
Volume:38
Page:6307-6308
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ISSN:0040-4039
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Container-title:Tetrahedron Letters
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language:en
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Short-container-title:Tetrahedron Letters
Author:
Grigg Ronald,Putnikovic Bogdan,Urch Christopher J
Subject
Organic Chemistry,Drug Discovery,Biochemistry
Reference5 articles.
1. Reviews: Cintas, P., Synthesis 1992, 248–257; Hodgson, D.M., J.Organomet.Chem., 1994, 476, 1–5; Saccomano, N.A., in Comprehensive Organic Synthesis, Trost, B.M., Fleming, I., Eds., Pergamon, Oxford, 1991, Vol. 1, pp. 173–209; Synthesis of natural products: Kishi, Y., Pure Appl. Chem. 1992, 64, 343–350; Nicolaou, K.C., Sorensen, E.J., Classics in Total Synthesis, VCH Publishers Inc., Weinheim, 1996, pp. 712–717 and references cited therein 2. Another approach uses stoichiometric excess of manganese powder as reducing agent and TMSCl as oxophilic species: Furstner, A., Shi, N., J.Am.Chem.Soc. 1996, 118, 2533–2534; Furstner, A., Shi, N., ibid 1996, 118, 12349–12357 3. For other examples of electrochemically driven transition metal mediated synthesis see reviews: Torii, S., Synthesis 1986, 873–886; Efimov, O.L., Strelets, V.V., Coord.Chem.Rev. 1990, 99, 15–53; Simonet, J., in Organic Electrochemistry, 3rd ed., Lund, H., Baizer, M.M., Eds., Marcel Dekker, Inc., New York, 1991, pp. 1217–1263; Bersier, P.M., Carlsson, L., Bersier, J., in Top.Curr.Chem., Steckhan, E., Ed., Springer-Verlag, Berlin, 1994, Vol. 170, pp. 113–143 4. Jin, H., Uenishi, J., Christ, W.J., Kishi, Y., J.Am.Chem.Soc. 1986, 108, 5644–5646; Takai, K., Tagashira, H., J.Am.Chem.Soc. 1986, 108, 6048–6050 5. General procedure: Electrolysis of the organic halide (1eq), aldehyde (1.2eq), CrCl2 (10mol%) and 0.1mol% Pd(OAc)2/0.4mol% PPH3 was performed in 0.1M LiClO4 in dry DMF, in a thermostatted divided H-type glass cell under constant current conditions (40mAcm−2). A carbon working electrode and a platinum auxiliary electrode were employed under a N2 atmosphere and reactions were run until t.l.c. monitoring showed the absence of starting material. Usual workup of the catholyte afforded the products (Table 1).
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