Addition compounds of alkali-metal hydrides. 24. A general method for preparation of potassium trialkoxyborohydrides. A new class of reducing agents

Brown, Herbert C.; Soon, Jin; Nazer, Behrooz

doi:10.1021/ic00187a006

Cited by 28 publications

(18 citation statements)

References 0 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…27 Among those higher derivatives, potassium triisopropoxyborohydride (KIPPBH) and potassium tri-s-butoxyborohydride show a high stereoselectivity, whereas the other derivatives show a much lower selectivity.…”

Section: (18)mentioning

confidence: 99%

“…ketone → alcohol (fast) acid chloride → reaction (slowly) carboxylic acid → no reduction ester → no reaction epoxide → no reaction amide → no reaction nitro compound → no reaction disulfide → thiol (fast) 27 other sulfur compound → no reaction Even though KIPBH is extremely mild reducing agent as described above, the reagent reduces disulfides to the corresponding thiols in essentially quantitative yields at a different reaction rate between aromatic and aliphatic disulfides: the reduction of aromatic disulfide is much faster than aliphatic one. Consequently, the former reduction is conveniently carried out at 0 o C (15 min), whereas, it is convenient to carry out the latter at 25 o C (5 h).…”

Section: (18)mentioning

confidence: 99%

“…Thus, only the aromatic nitrile is reduced selectively in an equimolar mixture of aromatic and aliphatic nitriles, 35 as in Eq. (27). Such a chemoselectivity between nitriles is classified as the first example in the literature.…”

mentioning

confidence: 98%

“…(26) (27) Potassium Dialkoxymonoalkylborohydrides. Generally, the products from simple boronic esters, KRB(OR') 2 H, undergo rapid redistribution.…”

mentioning

confidence: 99%

“…As mentioned earlier, diisobutylaluminum derivatives (17)(18)(19)(20)(21)(22)(23) 114, 122,124,125,126,140,[144][145][146][147][148] and diisopinocampheylboron derivatives (25)(26)(27)(28)(29)(30)(31)(32)(33) 132, [135][136][137]140,[149][150][151][152][153] have been applied to the regioselective reduction of α,β-unsaturated aldehydes and ketones. All the derivatives examined can reduce a variety of α,β-unsaturated aldehydes and ketones to the corresponding allylic alcohols, except Ipc 2 BOR 135-138, which can only reduce aldehydes but not attack ketones at all.…”

mentioning

confidence: 99%

See 4 more Smart Citations

Thirty Six Years of Research on the Selective Reduction and Hydroboration

Soon¹

2011

Bulletin of the Korean Chemical Society

View full text Add to dashboard Cite

thirty six years, the author and his collaborators have developed a variety of reducing and hydroborating agents, and applied them to organic synthesis, which involves the 1,2-reduction of α,β-unsaturated carbonyl compounds, stereoselective reduction of cycloalkanones, regioselective ring-opening of epoxides, partial reduction of carboxylic acid derivatives to aldehydes, regioselective addition to carbon-carbon multiple bonds, etc. by utilizing metal hydrides and the newly-devised the Meerwein-Ponndorf-Verley (MPV) type reagents. Such developments provide a new synthetic methodology making possible valuable selective reductions and hydroborations, not practical previously.

show abstract

Section: (18)mentioning

confidence: 99%

Section: (18)mentioning

confidence: 99%

mentioning

confidence: 98%

“…(26) (27) Potassium Dialkoxymonoalkylborohydrides. Generally, the products from simple boronic esters, KRB(OR') 2 H, undergo rapid redistribution.…”

mentioning

confidence: 99%