The different behavior of N-tosyl imines and N-(2-pyridyl)sulfonyl imines in Cu (II)-catalyzed AFCR is described. DFT theoretical calculations on the mode of coordination of the copper atom to both types of substrates allow understanding this different reactivity.
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Department of Chemistry, University of Warwick, Coventry, CV4 7AL, UK.
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Department of Chemistry, Indian Institute of Technology Bombay, Mumbai, 400 076, India.
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Catalytic synthesis of substituted 1,2-dihydronaphthalenes metalloradical activation of -styryl -tosyl hydrazones (()-2-(prop-1-en-1-yl)benzene--tosyl hydrazones) is presented, taking advantage of the intrinsic reactivity of a cobalt(iii)-carbene radical intermediate. The method has been successfully applied to a broad range of substrates with various substituents at the aromatic ring, producing the desired ring products in good to excellent isolated yields for substrates with an = COOEt substituent at the vinylic position (∼70-90%). Changing the moiety from an ester to other substituents has a surprisingly large influence on the (isolated) yields.
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