ChemInform Abstract: CDC Reactions of N‐Aryl Tetrahydroisoquinolines Using Catalytic Amounts of DDQ: C—H Activation under Aerobic Conditions.

Abstract

Cross dehydrogenative coupling of tetrahydroisoquinolines (I) and (VI) with enolizable ketones (II) and (IV) as well as phosphonates (VII), resp., proceeds efficiently in the presence of catalytic amounts of DDQ and AIBN (10 mol%). Only stoichiometric amounts of phosphonates are necessary. -(ALAGIRI, K.; DEVADIG, P.; PRABHU*, K. R.; Chem. Eur. J. 18 (2012) 17, 5160-5164, http://dx.

Evaluation of Phenyldiazenyl as a Protective/Activating Group in Lithiation–Substitution Reactions of Tetrahydroisoquinolines

“…16 In recent years, a variety of synthetic methods including transition-metal-catalyzed approaches, photocatalysis, and enzymatic transformations have been investigated for α-C–H elaboration of THIQs. 17 18 19 20 21 22 23 24 The method involving lithiation followed by electrophilic substitution is an attractive procedure to synthesize the C-1-substituted THIQs as it ensures regioselectivity. 25 This can be achieved either by prior BF 3 complexation in N-Me THIQs 26 27 28 or via functionalization of N-H THIQ using a protecting group like Boc, 29 30 31 oxazolines, 32 33 34 35 36 pivaloyl, 37 38 39 40 41 chiral formamidines, 42 43 44 and nitroso.…”