35216-11-6Relevant articles and documents
Visible-Light-Induced Nickel-Catalyzed Cross-Coupling with Alkylzirconocenes from Unactivated Alkenes
Bai, Songlin,Gao, Yadong,Jiang, Chao,Liu, Xiaolei,Qi, Xiangbing,Wang, Jing,Wu, Qingcui,Yang, Chao
, p. 675 - 688 (2020/03/11)
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Vinylic Organoboranes. 4. A General, One-Pot Synthesis of 6- and 7-Alkyn-1-ols via Boracyclanes. Influence of Steric Effects in the Iodination of Lithium Alkynyl "Ate" Complexes of Dialkylborinates
Brown, Herbert C.,Basavaiah, D.,Bhat, N. G.
, p. 4518 - 4521 (2007/10/02)
The iodination of the "ate" complexes derived from various B-alkoxyborinane derivatives and 1-alkynyllithium has been investigated.The results indicate the ate complex from B-methoxyborinane is converted into desired 6-alkyn-1-ol in a yield of only 22percent, with much larger amounts, 65percent, of the undesired 1-iodo-1-alkyne.Increases in the steric bulk of the alkoxy group on boron increase the yield of the required 6-alkyn-1-ol with the best results realized with B-(triphenylmethoxy)borinane.Treatment of B-(triphenylmethoxy)borinane with 1-alkynyllithium affords the corresponding "ate" complex.Subsequent iodination induces the migration of one end of the cycloalkyl chain from boron to the adjacent carbon, resulting in the formation of the one-carbon homologated borepane moiety.This then undergoes a rapid deiodoboronation to afford the corresponding (6-alkyn-1-yl)boronate ester.Oxidation of these esters produces the desired 6-alkyn-1-ols in excellent yields (85percent).An attempt to extend this reaction to di-n-alkylborinates to prepare the corresponding unsymmetrical alkynes did not achieve satisfactory results.Alternatively, the iodination of the "ate" complex from B-methylborinane and 1-alkynyllithium, followed by oxidation, provides the required 6-alkyn-1-ols in high yields.This procedure has been successfully extended to the seven-membered borepane moiety to provide the corresponding 7-alkyn-1-ols.Extension of this reaction to the di-n-alkylmethylboranes provides the corresponding unsymmetrical alkynes in good yields.Thus, these procedures constitute a simple, general and one-pot synthesis of the desired alkyn-1-ols, valuable synthons in organic synthesis.Insect pheromones, (Z)-7-tetradecenaland (Z)-7-hexadecenal, were readily prepared in excellent yields by utilizing this convenient procedure.
Long Chain Phenols. Part 19. The Synthesis of 3-phenol, 'Cardanol Monoene', and of 3-phenol, 'Cardanol Diene', and their Methyl Ethers
Caplin, Joseph,Tyman, John H. P.
, p. 321 - 351 (2007/10/02)
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