Hydroboration of alkynes using BH3 to give aldehydes
Description: When alkynes are treated with BH3 and subsequently treated with H2O2, they are converted into aldehydes.
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- THE HYDROBORATION OF ACETYLENES – A CONVENIENT CONVERSION OF INTERNAL ACETYLENES TO CIS OLEFINS OF HIGH PURITY AND OF TERMINAL ACETYLENES TO ALDEHYDES
Brown, H.C.; Zweifel, G. Am. Chem. Soc. 1959 81 (6), 1512 DOI: 10.1021/ja01515a058
The original paper describing the hydroboration of alkynes, by Nobel Laureate Prof. H. C. Brown (Purdue).
- PALLADIUM-CATALYZED REACTION OF 1-ALKENYLBORONATES WITH VINYLIC HALIDES: (1Z,3E)-1-PHENYL-1,3-OCTADIENE
Miayura, N.; Suzuki, A. Org. Synth. 1990, 68, 130 DOI:15227/orgsyn.068.0130
A procedure by Nobel Laureate Akira Suzuki for the hydroboration of an alkyne with catecholborane. The resulting product can then be subsequently used in a Pd-catalyzed Suzuki coupling reaction.
A variety of other reagents were developed by H. C. Brown for hydroboration, including catecholborane, 9-BBN, and disiamylborane. The advantage with these reagents is that they will undergo monoadditionto alkynes, whereas borane will add twice. Representative references for the reaction of these reagents with alkynes are below:
- Catecholborane (1,3,2-Benzodioxaborole) as a New, General Monohydroboration Reagent for Alkynes. A Convenient Synthesis of Alkeneboronic Esters and Acids from Alkynes via Hydroboration
Brown, H. C.; Gupta, S. K. Am. Chem. Soc. 1972 94 (12), 4370 DOI: 10.1021/ja00767a072
- 50. Hydroboration of Representative Alkynes with 9-Borabicyclo[3.3.1]nonane-a Simple Synthesis of Versatile Vinyl Bora and gem-Dibora Intermediates
Brown, H. C.; Scouten, C. G.; Liotta, R. J. Am. Chem. Soc. 1979 101 (1), 96 DOI:10.1021/ja00495a016
- XI. The Hydroboration of Acetylenes-A Convenient Conversion of Internal Acetylenes into cis-Olefins and of Terminal Acetylenes into Aldehydes
Brown, H. C.; Zweifel, G. J. Am. Chem. Soc. 1961, 83(18), 3834 DOI: 10.1021/ja01479a024
This paper describes the use of disiamylborane for the selective monohydroboration of alkynes.