Dicyclohexylborane

New Economical, Convenient Procedures for the Synthesis of Catecholborane

“…The catecholborane obtained after distillation using above-mentioned procedures has been stored at 0 °C, and no appreciable disproportionation was noted. However, when catecholborane was stored at room temperature, the amount of borate seemed to increase, similar to the observations made earlier 2c…”

“…This exchange presumably occurs via the transfer of the catechol moiety from >B−H to >B−R. In our earlier studies from this laboratory, we reported that trialkylboranes exchange the alkyl group with tri- O -phenylene bis-borate ( 2 ) in the presence of catalytic amounts of THF:BH 3 (eq 3) 2a …”

“…All manipulations and reactions with air-sensitive compounds were carried out in an inert atmosphere (dry nitrogen, argon, etc). The special techniques employed in handling air-sensitive materials are described elsewhere 2g…”

“…Catecholborane is one of the most versatile boron hydride reagents available for synthetic chemists. It has found a multitude of applications as a selective reducing and hydroborating agent . It has been effectively used in the preparation of alkyl- and alkenylboronic acids .…”

“…Although catecholborane can be prepared by other procedures, the preferred synthesis has been by the reaction of catechol with borane−tetrahydrofuran or borane−methyl sulfide (eq 1). 2a,

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