67753-90-6Relevant articles and documents
Copper-catalyzed γ-selective allyl-alkyl coupling between allylic phosphates and alkylboranes
Ohmiya, Hirohisa,Yokobori, Umi,Makida, Yusuke,Sawamura, Masaya
, p. 2895 - 2897 (2010)
(Figure Presented) Copper-catalyzed allyl-alkyl coupling between allylic phosphates and alkylboranes, prepared by hydroboration of alkenes with 9-BBN-H, takes place with complete γ- and E-selectivities and with preferential 1,3-anti stereochemistry. The reaction tolerates various functional groups in both the allylic phosphate and alkylborane. Catalytic mechanisms involving transmetalation between a trialkyl(alkoxo)borate and a copper(I) complex to form an alkylcopper(I) species are proposed. Copyright
Switchable Selectivity in the Pd-Catalyzed Alkylative Cross-Coupling of Esters
Masson-Makdissi, Jeanne,Vandavasi, Jaya Kishore,Newman, Stephen G.
supporting information, p. 4094 - 4098 (2018/07/15)
The Pd-catalyzed cross-coupling of phenyl esters and alkyl boranes is disclosed. Two reaction modes are rendered accessible in a selective fashion by interchange of the catalyst. With a Pd-NHC system, alkyl ketones can be prepared in good yields via a Suzuki-Miyaura reaction proceeding by activation of the C(acyl)-O bond. Use of a Pd-dcype catalyst enables alkylated arenes to be synthesized by a modified pathway with extrusion of CO. Applications of this divergent coupling strategy and the origin of the switchable selectivity are discussed.
Erratum: Preparation of imides via the palladium-catalyzed coupling reaction of organoborons with methyl N-[methoxy(methylthio)methylene]carbamate as a one-carbon elongation reaction (Organic Letters (2012) 14:24 (6294-6297) DOI: 10.1021/ol303062a)
Tomizawa, Takuhei,Orimoto, Kohei,Niwa, Takashi,Nakada, Masahisa
supporting information, p. 1535 - 1535 (2014/04/03)
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