Sequential directed ortho metalation-boronic acid cross-coupling reactions. A general regiospecific route to oxygenated dibenzo[b,d]pyran-6-ones related to ellagic acid

The Development of the Asymmetric Morita—Baylis—Hillman Reaction Catalyzed by Chiral Brønsted Acids

“…The addition of bromine at À 30 8C gave the 3,3'-dibromo cross-coupling partner 9 in 94% yield. [20] Using Suzuki reaction conditions as reported by Fu [23] or Snieckus [24] yielded the corresponding (R)-3,3'-diaryl-H 8 -BINOMe compounds 10a -d. Deprotection of the methyl ethers with boron tribromide at 0 8C gave catalysts 8a, b,d. Demethylation of 10c with boron tribromide was performed at À 78 8C to À 20 8C in order to avoid bromination of the highly activated 3,5-(bis-trifluoromethyl)phenyl group [25] yielding catalyst 8c.…”

Discovery of biphenyl-aryl ureas as novel VEGFR-2 inhibitors. Part 4: Exploration of diverse hinge-binding fragments

“…16 Then critical intermediate (5) was prepared from (2) and (3), or compound (1) and (4) by classical Pd-catalyzed Suzuki coupling reaction. 17 Finally, intermediate (5) was treated with triphosgene (BTC) to produce various isocyanate, followed by reacting with substituted anilines yielding the title compounds (L1-L9). 18 Compound (8) chloride in triethylamine.…”

“…The key intermediate (9) was prepared from (8) and (20) by Pd-catalyzed Suzuki coupling reaction. 17 Then, (9) was treated with triphosgene (BTC) to produce various isocyanate, followed by reacting with substituted anilines yielding the title compounds (W1-W12). 18 Compound (11) was synthesized from (10) by oxidizing reaction with KMnO 4 and acidification with hydrochloric acid.…”

The Suzuki Reaction with Arylboron Compounds in Arene Chemistry

“…A combination of Pd(PPh 3 ) 4 or PdCl 2 (PPh 3 ) 2 and aqueous Na 2 CO 3 in dimethoxyethane (DME) was reported to work satisfactorily in most cases [5,6].…”