Large-scale preparation of polyfunctional benzylic zinc reagents by direct insertion of zinc dust into benzylic chlorides in the presence of lithium chloride

Synthesis

Volumn , Issue 5, 2010, Pages 882-891

  Metzger, Albrecht ^a   Argyo, Christian ^a   Knochel, Paul ^a  

^a UNIVERSITY OF MUNICH   (Germany)

Author keywords

Benzylic zinc chlorides; Insertion; Lithium chloride; Zinc; Zinc organometallics

Indexed keywords

BENZYLIC; BENZYLIC ZINC CHLORIDES; INSERTION; LITHIUM CHLORIDE; ZINC CHLORIDE;

CHLORINE COMPOUNDS; DUST; LITHIUM;

ZINC;

BENZILIC ACID DERIVATIVE; ELECTROPHILE; LITHIUM CHLORIDE; ORGANOMETALLIC COMPOUND; POLYFUNCTIONAL GROUP; REAGENT; ZINC DERIVATIVE;

ARTICLE; CHEMICAL REACTION KINETICS; CHEMICAL STRUCTURE; CHEMOREACTIVITY; LARGE SCALE PRODUCTION; STOICHIOMETRY; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 77953233783     PISSN: 00397881     EISSN: 1437210X     Source Type: Journal    
DOI: 10.1055/S-0029-1217134     Document Type: Article

References (10)

1. (a) Knochel, P.; Singer, R. D. Chem. Rev. 1993, 93, 2117.
2. (b) Knochel, P.; Millot, N.; Rodriguez, A.; Tucker, C. E. Org. React. 2001, 58, 417.
3. (c) Knochel, P. In Handbook of Functionalized Organometallics; Wiley-VCH: Weinheim, 2005.
4. Krasovskiy, A.; Malakhov, V.; Gavryushin, A.; Knochel, P. Angew. Chem. Int. Ed. 2006, 45, 6040.
5. Metzger, A.; Schade, M. A.; Knochel, P. Org. Lett. 2008, 10, 1107.
6. Stoll, A. H.; Krasovskiy, A.; Knochel, P. Angew. Chem. Int. Ed. 2007, 46, 606.
7. Yield indicated by iodometric titration; see also: Krasovskiy, A.; Knochel, P. Synthesis 2006, 890.
8. Knochel, P.; Yeh, M. C. P.; Berk, S. C.; Talbert, J. J. Org. Chem. 1988, 53, 2390.
9. Villieras, J.; Rambaud, M. Synthesis 1982, 924.
10. According to: Berk, S. C.; Yeh, M. C. P.; Jeong, N.; Knochel, P. Organometallics 1990, 9, 3053.