7693-84-7Relevant articles and documents
Catalyst-Controlled 1,2- and 1,1-Arylboration of α-Alkyl Alkenyl Arenes
Bergmann, Allison M.,Dorn, Stanna K.,Smith, Kevin B.,Logan, Kaitlyn M.,Brown, M. Kevin
supporting information, p. 1719 - 1723 (2019/01/14)
Two methods are reported for the 1,2- and 1,1-arylboration of α-methyl vinyl arenes. In the case of 1,2-arylboration, the formation of a quaternary center occurred through a rare cross-coupling reaction of a tertiary organometallic complex. 1,1-Arylboration was enabled by catalyst optimization and occurred through a β-hydride elimination/reinsertion cascade. Enantioselective variants of both processes are presented as well as mechanistic investigations.
Enantioselective CuH-Catalyzed Reductive Coupling of Aryl Alkenes and Activated Carboxylic Acids
Bandar, Jeffrey S.,Ascic, Erhad,Buchwald, Stephen L.
supporting information, p. 5821 - 5824 (2016/06/09)
A new method for the enantioselective reductive coupling of aryl alkenes with activated carboxylic acid derivatives via copper hydride catalysis is described. Dual catalytic cycles are proposed, with a relatively fast enantioselective hydroacylation cycle followed by a slower diastereoselective ketone reduction cycle. Symmetrical aryl carboxyclic anhydrides provide access to enantioenriched α-substituted ketones or alcohols with excellent stereoselectivity and functional group tolerance.
Role of free space and conformational control on photoproduct selectivity of optically pure α-alkyldeoxybenzoins within a water-soluble organic capsule
Kulasekharan, Revathy,Maddipatla, Murthy V. S. N.,Parthasarathy, Anand,Ramamurthy
, p. 942 - 949 (2013/04/10)
Optically pure α-alkyl deoxybenzoins resulting in products of Norrish Type I and Type II reactions upon excitation has been investigated within the octa acid (OA) capsule in water. The product distribution was different from that in an organic solvent and was also dependent on the length of the α-alkyl chain. Most importantly, a rearrangement product not formed in an organic solvent arising from the triplet radical pair generated by Norrish Type I reaction was formed, and its yield was dependent on the alkyl chain length. In an organic solvent, since the cage lifetime is shorter than the time required for intersystem crossing (ISC) of the triplet radical pair to the singlet radical pair the recombination with or without rearrangement of the primary radical pair (phenylacetyl and benzyl) does not occur. Recombination without rearrangement within the capsule as inferred from monitoring the racemization of the optically pure α-alkyl deoxybenzoins suggesting the capsule's stability for at least 10-8 s (the time required for ISC) is consistent with our previous photophysical studies that showed partial opening and closing of the capsule in the time range of microseconds.
