Hydroxymethylation of organic halides. Evaluation of a catalytic system involving a fluorous tin hydride reagent for radical carbonylation

Tetrahedron Letters

Volumn 38, Issue 45, 1997, Pages 7883-7886

  Ryu, Ilhyong ^a   Niguma, Tatsuro ^a   Minakata, Satoshi ^a   Komatsu, Mitsuo ^a   Hadida, Sabine ^b   Curran, Dennis P ^b  

^a OSAKA UNIVERSITY   (Japan)

^b UNIVERSITY OF PITTSBURGH   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CARBONYL DERIVATIVE; ORGANOHALOGEN DERIVATIVE; TIN;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CYCLIZATION; METHYLATION; PROTON TRANSPORT; STOICHIOMETRY;

EID: 0030830706     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)10076-4     Document Type: Article

References (11)

1. Curran, D. P.; Hadida, S. J. Am. Chem. Soc. 1996, 118, 2531-2532.
2. For a review, see: (a) Ryu, I.; Sonoda, N. Angew. Chem., Int. Ed. Engl. 1996, 35, 1050-1066.
3. Also see a review including radical C1 synthons: (b) Ryu, I.; Sonoda, N.; Curran, D. P. Chem. Rev. 1996, 96, 177-206.
4. 3CN system, see: Gupta, V.; Kahne, D. Tetrahedron Lett. 1993, 34, 591-594.
5. Ryu, I.; Kusano, K.; Ogawa, A.; Kambe, N.; Sonoda, N. J. Am. Chem. Soc. 1990, 112, 1295-1297.
6. For TTMSS mediated system, see: Ryu, I.; Hasegawa, M.; Kurihara, A.; Ogawa, A.; Tsunoi, S.; Sonoda, N. Synlett 1993, 143-145.
7. Horner, J. H.; Martinez, F. N.; Newcomb, M.; Hadida, S.; Curran, D. P. Tetrahedron Lett. 1997, 38, 2783-2786.
8. Stork, G.; Sher, P. M. J. Am. Chem. Soc. 1986, 108, 303-304.
9. For use of BTF, see: Ogawa, A.; Curran, D. P. J. Org. Chem. 1997, 62, 450-451.
10. 3CN/t-BuOH at 80 °C gave dodecane in 10-20% yield.
11. Cf.: For easy separation of conventional tributyltin hydride via in situ reduction, see: Crich, D.; Sun, S. J. Org. Chem. 1996, 61, 7200-7201.