Pd(PPh)Cl-catalyzed selective tandem cyclization/oxidation of available conjugated diazo ene-yne-ketones under O atmosphere led to the formation of diazo trisubstituted furans. The Rh(OAc)-mediated selective C(sp)-H insertion at the ortho-position of 2-aryl group (R) of the furan moiety under N atmosphere occurred to construct naphthalene cycle, affording trifunctionalized naphtho[1,2- b]furans. C(sp)-H insertion at the 4-position of the furan ring, and Wolf rearrangement of diazo moiety have not been observed.
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Synthesis of Trifunctionalized Naphtho[1,2- b]furans Based on the Strategy for the Construction of Both Furan and Naphthalene Cycle.
J Org Chem
May 2019
Key Laboratory of Chemical Biology and Traditional Chinese Medicine Research (Ministry of Education of China) and Key Laboratory of the Assembly and Application of Organic Functional Molecules of Hunan Province , Hunan Normal University, Changsha 410081 , China.
Pd(PPh)Cl-catalyzed selective tandem cyclization/oxidation of available conjugated diazo ene-yne-ketones under O atmosphere led to the formation of diazo trisubstituted furans. The Rh(OAc)-mediated selective C(sp)-H insertion at the ortho-position of 2-aryl group (R) of the furan moiety under N atmosphere occurred to construct naphthalene cycle, affording trifunctionalized naphtho[1,2- b]furans. C(sp)-H insertion at the 4-position of the furan ring, and Wolf rearrangement of diazo moiety have not been observed.
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