Boronic carbonyl compound arylation

After these seminal studies, the use of NHC-Rh systems for the addition of aryl boronic acids to carbonyl compounds became a very fertile area and many groups have reported on variations of this catalytic system [22],... 

Scheme 7.5 NHC-Pd and NHC-Ni catalysed arylation of carbonyls compounds with boron reagents...

In 1990 Alper and Lee reported on a cobalt-catalyzed carbonylation of aryl iodides and alkyl iodides [293, 294]. In the presence of cobalt chloride or acetate, potassium cyanide, base, and PEG-400, carboxylic acids were produced from the corresponding iodo compounds. Lewis acids, such as boron trifluoride etherate... 

Scheme 5.23 Palladium(ll)-catalyzed 1,4-addition of aryl boron compounds to a,p-unsaturated carbonyl compounds, as described by Miyaura and coworkers [73].

Lewis acid-catalyzed addition of carbonyl compounds to alkenes is an important method for forming new carbon-carbon bonds. Lewis acid-promoted ene and Baylis-Hillman reactions have been well documented. Notably, boron trihalide-mediated aryl aldehyde-styrene coupling reactions proceed in a different way (Scheme 23.17). Boron trihalide acts simultaneously as a Lewis acid and as a reactant to regioselectively produce l,3-dihalo-l,3-diarylpropane (synlanti = 50/50). 

Cross-coupling reactions 5-alkenylboron boron compounds, 9, 208 with alkenylpalladium(II) complexes, 8, 280 5-alkylboron boron, 9, 206 in alkyne C-H activations, 10, 157 5-alkynylboron compounds, 9, 212 5-allylboron compounds, 9, 212 allystannanes, 3, 840 for aryl and alkenyl ethers via copper catalysts, 10, 650 via palladium catalysts, 10, 654 5-arylboron boron compounds, 9, 208 with bis(alkoxide)titanium alkyne complexes, 4, 276 carbonyls and imines, 11, 66 in catalytic C-F activation, 1, 737, 1, 748 for C-C bond formation Cadiot-Chodkiewicz reaction, 11, 19 Hiyama reaction, 11, 23 Kumada-Tamao-Corriu reaction, 11, 20 via Migita-Kosugi-Stille reaction, 11, 12 Negishi coupling, 11, 27 overview, 11, 1-37 via Suzuki-Miyaura reaction, 11, 2 terminal alkyne reactions, 11, 15 for C-H activation, 10, 116-117 for C-N bonds via amination, 10, 706 diborons, 9, 167... 

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