Electrochemically driven catalytic Pd(0)/Cr(II) mediated coupling of organic halides with aldehydes. The Nozaki-Hiyama-Kishi reaction

Tetrahedron Letters

Volumn 38, Issue 35, 1997, Pages 6307-6308

  Grigg, Ronald ^a   Putnikovic, Bogdan ^a   Urch, Christopher J ^b  

^a UNIVERSITY OF LEEDS   (United Kingdom)

^b JEALOTT S HILL RESEARCH STATION   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; ORGANOHALOGEN DERIVATIVE; PALLADIUM COMPLEX;

ARTICLE; CATALYSIS; CHEMICAL REACTION; ELECTRODE; REACTION ANALYSIS; SYNTHESIS;

EID: 0030744538     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)01415-9     Document Type: Article

References (14)

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. 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
3. 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
4. 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
5. 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
6. 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
7. 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
8. rd 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
9. rd 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
10. rd 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
11. rd 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
12. 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
13. 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
14. 2 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).