Development of fluorinated benzils and bisbenzils as room-temperature phosphorescent molecules

• Shigeyuki Yamada,
• Takuya Higashida,
• Yizhou Wang,
• Masato Morita,
• Takuya Hosokai,
• Kaveendra Maduwantha,
• Kaveenga Rasika Koswattage and
• Tsutomu Konno

Beilstein J. Org. Chem. 2020, 16, 1154–1162, doi:10.3762/bjoc.16.102

• materials. Keywords: alkyne oxidation; benzils; bistolanes; fluorinated compounds; phosphorescence; Introduction The development of organic light-emitting molecules is recognized as one of the most important studies because of the broad application of these compounds as fluorescence probes, bio-imaging

• pathway for fluorinated benzil (2) and bisbenzil (3) derivatives. Proposed mechanism of Pd(II)-catalyzed alkyne oxidation by dimethyl sulfoxide (DMSO). Photophysical data from ultraviolet (UV)-visible absorption and steady-state photoluminescence (PL) measurementsa. Supporting Information Experimental

Gold-catalyzed regioselective oxidation of propargylic carboxylates: a reliable access to α-carboxy-α,β-unsaturated ketones/aldehydes

• Kegong Ji,
• Jonathan Nelson and
• Liming Zhang

Beilstein J. Org. Chem. 2013, 9, 1925–1930, doi:10.3762/bjoc.9.227

• anticipated isomer 5a’, accessible via the gold carbene B’ from a regioisomeric alkyne oxidation, was not positively detected due to the trace amount (<0.5%), thereby revealing an exceptional level of regioselectivity in the oxidation of this type of internal alkynes. The formations of 5a-OAc and 5a-H are

• migration might be an even less meaningful event in the reaction; b) it is known that the gold carbenes of type B can be readily oxidized by Ph2S=O [33], which, however, is an inefficient oxidant for generating α-oxo gold carbenes of type A via alkyne oxidation [34][35]; when the N-oxide 3 is replaced by

• a tris-coordinated gold complex (i.e., D) [11]. The scope of this alkyne oxidation/acetoxy migration reaction is outlined in Table 1. Acetates derived from primary/secondary propargylic alcohols with various substitution patterns and containing different functional groups were all allowed, although

Gold-catalyzed regioselective oxidation of terminal allenes: formation of α-methanesulfonyloxy methyl ketones

• Yingdong Luo,
• Guozhu Zhang,
• Erik S. Hwang,
• Thomas A. Wilcoxon and
• Liming Zhang

Beilstein J. Org. Chem. 2011, 7, 596–600, doi:10.3762/bjoc.7.69

• is proposed in Scheme 3. The first step, as in the case of alkyne oxidation [22][23][25], is probably an attack by the pyridine N-oxide on the gold-activated allene. Selective reaction at the terminal C–C double bond should occur due to steric preference. The allyl gold intermediate E can then