57378-74-2

Upstream product

• 676541-38-1 (2-bromophenyl)(cyclopropyl)methanone 
• 7154-66-7 2-bromobenzoic acid chloride 
• 939-87-7 2-phenyl-1-cyclopropanecarbonyl chloride 
• 5771-62-0 1a,6a-Dihydro-1H-cyclopropainden-6-one 
• 75-11-6 diiodomethane 
• 61463-21-6 3-Hydroxyindene 

Downstream Products

• 61463-14-7 3,5-Dinitro-benzoic acid (1aR,6S,6aS)-(1,1a,6,6a-tetrahydro-cyclopropa[a]inden-6-yl) ester 
• 61463-14-7 3,5-Dinitro-benzoic acid (1aR,6R,6aS)-(1,1a,6,6a-tetrahydro-cyclopropa[a]inden-6-yl) ester 

Relevant academic research and scientific papers

Synthesis of 1-indanols and 1-indanamines by intramolecular palladium(0)-catalyzed C(sp3)-H arylation: Impact of conformational effects

A range of valuable 1-indanols and 1-indanamines containing a tertiary C1 atom were synthesized by intramolecular palladium(0)-catalyzed C(sp 3)-H arylation, despite unfavorable steric interactions. The efficiency of the reaction was found to correlate with the degree of substitution at C2, as expected from the Thorpe-Ingold effect. Additionally, the nature of the heteroatomic substituent at C1 had a marked influence on the diastereoselectivity at C1 and C2; indeed, 1-indanols and 1-indanamines were obtained with the opposite relative configuration. Analysis of the X-ray and DFT-optimized structures of the corresponding reactive intermediates provided useful insights into the subtle conformational effects induced by these substituents.