Reactivity and selectivity of ortho-metalated Rhodium(II) complexes in C-H insertion reactions of alpha-diazo compounds | Health & Environmental Research Online (HERO)

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Citation
Tags

HERO ID

7267896

Reference Type

Journal Article

Title

Reactivity and selectivity of ortho-metalated Rhodium(II) complexes in C-H insertion reactions of alpha-diazo compounds

Author(s)

Estevan, F; Lahuerta, P; Perez-Prieto, J; Pereira, I; Stiriba, SE; ,

Year

1998

Is Peer Reviewed?

Journal

Organometallics
ISSN: 0276-7333
EISSN: 1520-6041

Publisher

AMER CHEMICAL SOC

Location

WASHINGTON

Page Numbers

3442-3447

Web of Science Id

WOS:000075378500010

Abstract

Regioselective intramolecular C-H insertion reactions of alpha-diazo beta-keto esters and cc-diazo ketones are mediated by Rh-2[OOCR](4-x)[PC](x), (x = 1, 2; PC = ortho-metalated phosphine; R = CH3, C3F7). In particular, the intramolecular transformation of 1-diazo-5-methyl-3 -propyl-2-hexanone catalyzed by Rh-2[OOCCH3](2)[PC](2) (PC = (C6H4)P(C6H5)(2), head-to-tail (H-T) configuration) afforded only the tertiary C-H insertion product. By comparison, no C-H insertion reaction was promoted by doubly metalated complexes with a head-to-head (H-H) configuration. Rh-2[OOCR](3)[PC] compounds were found to be less suited for these type of reactions.