Rhodium-catalyzed carbonylative arylation of alkynes with arylboronic acids: an efficient and straightforward method in the synthesis of 5-aryl-2(5H)-furanones

Nickel(0)-Catalyzed Formation of Oxaaluminacyclopentenes via an Oxanickelacyclopentene Key Intermediate: Me2AlOTf-Assisted Oxidative Cyclization of an Aldehyde and an Alkyne with Nickel(0)

“…Spectral data for 5a : 1 H NMR (270 MHz, CDCl 3 , rt, δ/ppm) 6.27 (s, 1H, −C(O)OC H Ph−), 7.1−7.6 (m, 15H, Ph ); 13 C{ 1 H} NMR (100 MHz, CDCl 3 , rt, δ/ppm) 83.9 (−COO C HPh−), 127.1 ( Ph ), 127.9 (−COC(Ph) C (Ph)−), 128.6 ( Ph ), 128.8 ( Ph ), 128.9 ( Ph ), 129.1 ( Ph ), 129.2 ( Ph ), 129.60 ( Ph ), 129.64 ( Ph ), 130.06 ( Ph ), 130.09 ( Ph ), 131.4 ( Ph ), 135.0 ( Ph ), 159.5 (−CO C (Ph)C(Ph)−), 172.7 (− C OC(Ph)C(Ph). These 1 H and 13 C chemical shift values were found to be almost identical to reported values . HRMS (EI): calcd for C 22 H 16 O 2 312.1150, found m / z 312.1154.…”

Rh(I)-Catalyzed CO Gas-Free Carbonylative Cyclization Reactions of Alkynes with 2-Bromophenylboronic Acids Using Formaldehyde

“…Consequently, gaseous carbon monoxide has been replaced by much easier handling organic and inorganic carbonyl compounds in various carbonylation reactions, as follows: hydrocarbonylation (hydroesterification, hydroamidation, and hydrocarboxylation) of alkenes and alkynes; , hydroformylation of alkenes; alkoxy-, amino-, and hydroxycarbonylation of aromatic and alkenyl halides; , the Pauson−Khand reaction; , hydrocyclocarbonylation of alkynes; , and carbonylative ring-expansion of spiropentanes . In this paper, we describe a new utilization of the CO gas-free protocol consisting of decarbonylation of formaldehyde and sequential carbonylation; ,,,, thus, a rhodium(I)-catalyzed carbonylative cyclization reaction of alkynes with 2-haloboronic acids in the presence of formaldehyde results in carbonylative cyclization to afford indenones. , …”

Rhodium-Catalyzed Carbonylative Synthesis of Heterocycles

“…Aryl boronic reagents can be carbonylated with rhodium catalysts to give acyl rhodium species that are amenable to the addition of unsaturated C-C bonds [88][89][90][91][92][93][94]. In 2009 Artok and co-workers investigated a carbonylative reaction of various alkynes with aryl boronic acids in the presence of Rh complex and afforded 5-aryl-2 (5H )-furanones (Scheme 42) [95].…”