Arylboronic acids [Ar-B(OH)2] are very useful precursors used in Pd-catalyzed Suzuki Couplings, where almost any organic halide can be coupled with an arylboronic acid, one example being that allyl bromide would give allylbenzenes.
(https://www.thevespiary.org/rhodium/Rhodium/hive/hiveboard/picproxie_docs/000433965-file_yobe.gif)
General procedure for arylboronic acid synthesis1
Magnesium turnings (30 mmol) were placed in a round-bottomed flask and then flame-dried under N2. Aryl bromide (30 mmol) dissolved in THF (20 mL) was added with an addition funnel to the flask slowly. The reaction mixture was gently refluxed for 3 to 4 h. After cooling, the Grignard reagent was transferred to a solution of (CH3O)3B in THF (10 mL) at -78°C and stirred overnight while warming up to RT slowly. After acidification with 10% HCl (10 mL), the product was extracted into ether (3x100 mL) and dried (sodium sulfate). The solvent was then removed under reduced pressure, and the products was precipitated by hexane with further recrystallization from water.
p-Tolylboronic acid: white needles were obtained in 81% yield; mp 243-244°C (lit.2 242-243°C).
p-Methoxyphenylboronic acid: White needles were obtained in 72% yield; mp 197-198°C (lit.2 202-205°C).
Arylboronic Acid References:
[1]: Tetrahedron 51(11), 3129 (1995)
[2]: J. Am. Chem. Soc. 53, 711 (1931)
Suzuki Coupling
In this reaction is a bromo compound R-Br coupled to a boronic acid R'-B(OH)2 with Pd-catalyst. In the first step the bromo compound is added oxidative at Pd(0) and the bomide is metathetically substituted by an hydroxy ion. After trans-metallation and secession of tetrahydroxyborate the Pd(II) with both organic moieties is obtained. The Pd is reductively eliminated and the residues coupled to R-R'.
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Suzuki Coupling References:
http://themerckindex.cambridgesoft.com/TheMerckIndex/NameReactions/ONR388.htm (http://themerckindex.cambridgesoft.com/TheMerckIndex/NameReactions/ONR388.htm)
http://www.chempensoftware.com/reactions/rxn566.htm (http://www.chempensoftware.com/reactions/rxn566.htm)
http://www.mdpi.net/ecsoc-5/e0029/e0029.htm (http://www.mdpi.net/ecsoc-5/e0029/e0029.htm)
http://www.sigmaaldrich.com/img/assets/3460/al_arylboronic_acids.pdf (http://www.sigmaaldrich.com/img/assets/3460/al_arylboronic_acids.pdf)
Suzuki couplings can be close to quantitative in some cases (where degassed solvents, inert atmosphere, fancy Pd ligands and reactive substrates are used), but expect good yields, as in 75%+ or so for non-problematic substrates.
Below are two Suzuki couplings I have posted here earlier, I'm sure you can find more using TFSE, and if you search for "suzuki coupling" or "suzuki reaction" using Google, you'll find a lot of articles on the topic.
Post 320892 (missing)
(Rhodium: "Allylbenzenes by Suzuki Coupling", Novel Discourse)
Post 405016 (https://www.thevespiary.org/talk/index.php?topic=11779.msg40501600#msg40501600)
(Rhodium: "Pd-catalyzed Suzuki synth of phenylacetamides", Novel Discourse)
No hard feelings, I merely thought that you might find more info on google than from me, my palladium coupling chem knowledge could be a lot better than it is.
I found a few review articles about Suzuki Chemistry today:
Chem. Rev. 95, 2457 (1995) (https://www.thevespiary.org/rhodium/Rhodium/pdf/pd-cat.cross-coupling.organoborons.pdf)
(https://www.thevespiary.org/rhodium/Rhodium/pdf/pd-cat.cross-coupling.organoborons.pdf)
J. Organomet. Chem. 576, 147 (1999) (https://www.thevespiary.org/rhodium/Rhodium/pdf/suzuki.cross-coupling.review.1995-1998.pdf)
(https://www.thevespiary.org/rhodium/Rhodium/pdf/suzuki.cross-coupling.review.1995-1998.pdf)
Chem. Rev. 102, 1359 (2002) (https://www.thevespiary.org/rhodium/Rhodium/pdf/aryl-aryl.bond-formation.pdf)
(https://www.thevespiary.org/rhodium/Rhodium/pdf/aryl-aryl.bond-formation.pdf)