Spangler, Jillian E. published the artcileα-Arylation of Saturated Azacycles and N-Methylamines via Palladium(II)-Catalyzed C(sp3)-H Coupling, COA of Formula: C14H12BNO4S, the publication is Journal of the American Chemical Society (2015), 137(37), 11876-11879, database is CAplus and MEDLINE.
In the presence of Pd(O2CCF3)2, N-(thiopivaloyl) nitrogen heterocycles such as I (R = H; X = CH2, CH2CH2CH2) underwent chemoselective and regioselective arylation with arylboronic acids R1B(OH)2 (R1 = Ph, 2-MeC6H4, 3-MeC6H4, 4-MeC6H4, 3-MeOC6H4, 4-MeOC6H4, 4-AcNHC6H4, 4-F3COC6H4, 3,4-Cl2C6H3, 4-ClC6H4, 3-ClC6H4, 2-FC6H4, 4-FC6H4, 4-F3CC6H4, 4-AcC6H4, 3-AcC6H4, 5-benzofuranyl, 1-PhSO2-4-indolyl, 1-PhSO2-5-indolyl, 6-F-3-pyridinyl, 2-F-4-pyridinyl, 6-Cl-3-pyridinyl, 6-MeO-3-pyridinyl, 2-MeO-4-pyridinyl) mediated by 1,4-benzoquinone in tert-amyl alc. with KHCO3 to give monoarylated heterocycles such as (thiopivaloyl)arylpyrrolidines I (R = R1; R1 = Ph, 2-MeC6H4, 3-MeC6H4, 4-MeC6H4, 3-MeOC6H4, 4-MeOC6H4, 4-AcNHC6H4, 4-F3COC6H4, 3,4-Cl2C6H3, 4-ClC6H4, 3-ClC6H4, 2-FC6H4, 4-FC6H4, 4-F3CC6H4, 4-AcC6H4, 3-AcC6H4, 5-benzofuranyl, 1-PhSO2-4-indolyl, 1-PhSO2-5-indolyl, 6-F-3-pyridinyl, 2-F-4-pyridinyl, 6-Cl-3-pyridinyl, 6-MeO-3-pyridinyl, 2-MeO-4-pyridinyl; X = CH2) and (thiopivaloyl)phenylhexahydroazepine I (R = Ph; X = CH2CH2CH2). Unsym. trans-2,5-diaryl-1-(thiopivaloyl)pyrrolidines were prepared in >20:1 dr in one pot using this method. Tertiary N-methylthiopivalamides t-BuC(:S)N(Me)R2 (R2 = Me, n-Pr, PhCH2, PhCH2CH2, cyclohexyl, Ph, 4-FC6H4, 4-ClC6H4) underwent chemoselective and regioselective arylation with arylboronic acids (R3 = Ph, 1-PhSO2-5-indolyl, 5-benzofuranyl, 6-MeO-3-pyridinyl) under similar conditions to yield (arylmethyl)thiopivalamides t-BuC(:S)N(CH2R3)R2 (R2 = Me, n-Pr, PhCH2, PhCH2CH2, cyclohexyl, Ph, 4-FC6H4, 4-ClC6H4; R3 = Ph, 1-PhSO2-5-indolyl, 5-benzofuranyl, 6-MeO-3-pyridinyl). The structure of a trans-(fluorophenyl)(methoxyphenyl)thiopivaloylpyrrolidine was determined by X-ray crystallog.
Journal of the American Chemical Society published new progress about 480438-51-5. 480438-51-5 belongs to indole-building-block, auxiliary class Indole,Boronic acid and ester,Sulfamide,Benzene,Boronic Acids,Boronic Acids,Boronic acid and ester,, name is (1-(Phenylsulfonyl)-1H-indol-5-yl)boronic acid, and the molecular formula is C6H3ClFNO2, COA of Formula: C14H12BNO4S.
Referemce:
https://www.nature.com/articles/s41429-020-0333-2,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles