Formation of the Tertiary Sulfonamide C(sp3)–N Bond Using Alkyl Boronic Ester via Intramolecular and Intermolecular Copper-Catalyzed Oxidative Cross-Coupling

8,8′-(Benzo[c][1,2,5]thiadiazole-4,7-diyl)bis(quinolin-4(1H)-one): a twisted photosensitizer with AIE properties

RSC Advances ◽

10.1039/d1ra06263h ◽

2021 ◽

Vol 11 (47) ◽

pp. 29102-29107

Author(s):

Emmanouil Broumidis ◽

Callum M. S. Jones ◽

Maria Koyioni ◽

Andreas Kourtellaris ◽

Gareth O. Lloyd ◽

...

Keyword(s):

Cross Coupling ◽

Boronic Ester

A new benzothiadiazole (BTZ) luminogen is prepared via the Suzuki–Miyaura Pd-catalysed C–C cross-coupling of 8-iodoquinolin-4(1H)-one and a BTZ bispinacol boronic ester.

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The Synthesis of Biarylmonophosphonates via Palladium-Catalyzed Phosphonation, Iridium-Catalyzed C-H Borylation, Palladium-Catalyzed Suzuki–Miyaura Cross-Coupling

Catalysis Letters ◽

10.1007/s10562-021-03643-3 ◽

2021 ◽

Author(s):

Simon Doherty ◽

Julian G. Knight ◽

Tina S. T. Tran ◽

Hussam Y. Alharbi ◽

Daniel O. Perry

Keyword(s):

Cross Coupling ◽

Statistical Mixture ◽

Boronic Ester ◽

Synthetic Procedure ◽

Boronic Esters ◽

Palladium Catalyzed ◽

Nucleophilic Reagents ◽

Sole Product

Abstract The iridium-catalyzed C-H borylation of diethyl phenylphosphonate results in nonselective mono and bisborylation to afford a near statistical mixture of 3-, 3,5- and 4-boryl substituted aryl phosphonates whereas 3-substituted aryl phosphonates undergo highly regioselective C-H borylation to afford the corresponding meta-phosphonate substituted arylboronic esters as the sole product; the resulting boronic esters were used as nucleophilic reagents in a subsequent palladium-catalyzed Suzuki–Miyaura cross-coupling to generate a range of biarylmonophosphonates. Gratifyingly, the Suzuki–Miyaura cross-coupling can be conducted without purifying the boronic ester which greatly simplifies the synthetic procedure. Graphical Abstract

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Cu-Catalyzed cis-selective ring-opening cross-coupling of an oxabicyclic olefin with an organoboron reagent

Organic & Biomolecular Chemistry ◽

10.1039/d0ob02557g ◽

2021 ◽

Vol 19 (7) ◽

pp. 1493-1497

Author(s):

Bowen Liu ◽

Guochun Peng ◽

Yu Zhang ◽

Chunhui Liu ◽

Jinbo Zhao

Keyword(s):

Ring Opening ◽

Cross Coupling ◽

Dft Studies ◽

Rate Determining Step ◽

Boronic Ester ◽

Selective Ring Opening

Cu(i)-Catalyzed cis-selective ring-opening of an oxabicyclic olefin with an organoboron reagent is described. DFT studies revealed an alternative boronic ester assisted non-canonical β-oxygen elimination as the rate-determining step.

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