Organoborane chemistry

Onak, T. Organoborane Chemistry Academic Press New York, 1975 p. 13. 

G. A. Olah, G. K. Surya Prakash, R. E. Williams, L. D. Field, K. Wade, Hypercarbon Chemistry, Wiley, New York, 1987 E. Muetterties, Boron Hydride Chemistry, Academic Press, New "Vbrk, 1975 R. N. Grimes, Carboranes, Academic Press, New York, 1970 T. Onak, Organoborane Chemistry, Academic Press, New York, 1975 V I. Bregadze, Chem. Rev., 92, 209 (1992). 

Two new syntheses of bombykol (6), the female sex pheromone of the silkworm moth (Bombyx mori), were reported [22,23]. Scheme 11 shows Negishi s synthesis of 6 based on organoborane chemistry [22], and Uenishi s synthesis of 6 based on palladium and nickel catalyses is summarized in Scheme 12 [23]. Both syntheses afforded bombykol of >98% purity. 

T. Onak, Organoborane Chemistry , Academic Press, New York, 1975. 

Interesting similarities can be advanced between nickel catalyzed hydrocyana> tion and hydroboration [181 reactions (the isomerization step being related to borane isomerization througli elirrunation-addition reactions), the drift of nickel toward the less hindered terminal position being genuinely reminiscent of organoborane chemistry. 

Brown, H. C., Rangaishenvi, M. V. Some recent applications of hydroboration/organoborane chemistry to heterocycles. J. Heterocycl. 

Bombykol M H / c - c n n-Pr (CfklyfJH Silkworm molh Bomhyx mori) Ks Organoborane chemistry I47 ... 

SHpsenol /UUU Bark beetles (//J.v) A Organoborane chemistry, L-proline-catalyzed asymmetric aldol reaction [I48r [166J"... 

Slegohlmirte (2S,3S,5R)- Trimethyl-6-(l- methyl-2-oxo- propyl)-2,3- clihydrapyran-4- one Drugstore beetle (Slegobiiim paitic-eum) Fs Organoborane chemistry Titanium(IV) chloride -Sharpless asymmetric epoxidation [150] [160]"... 

T. Onak, Organoborane Chemistry. Academic Press. London (1975) G. Wilkinson, F. G. A. Stone. E. W. Abel, Comprehensive Organometallic Chemistrw Vol. 1, Pergamon Press. Oxford (1982). 

Two important works were reported by others in the 1990s. First, Oppolzer in Switzerland found that the intramolecular cyclization as shown in D 114 of Figure 4.71 could best be accomplished with titanium tetrachloride in the presence of ethyldiisopropylamine in dichloromethane at —78 °C.125 Then, Matteson in the USA synthesized pure and crystalline (25,35,17 )-114 by employing his organoborane chemistry.126 This prompted us to attempt our second synthesis of (25,35,1 5)-114 to obtain it as crystals. 

Hara T, Yuasa M (1999). Automated synthesis of [nC] Choline, a positron-emitting tracer for tumor imaging. Appl Radiat Isot 50 531 Huisman MC, Higuchi T, Reder S et al (2008). Initial characterization of an 18F-labled myocardial perfusion tracer. J Nucl Med 49 630 Kabalka GW, Lambrecht RM, Fowler JS et al (1985). Synthesis of 150-labelled butanol via organoborane chemistry. Appl Radiat Isot 36 853 Kamarainen EL, Kyllonen T, Nihtila O et al (2004). Preparation of fluorine-18 labeled fluoromisonidazole using two different synthesis methods. J Labeled Comp Radiopharm 47 37... 

Ichikawa et al. (55) have reported a general procedure for the synthesis of hydrocarbons substituted with a terminal difluoroolefin (Scheme 38). Elimination of HF from the tosylate 127 afforded a lithium species 128 which was elaborated to 129 using organoborane chemistry. The yields were generally good but the nature of the reaction precludes many functional groups. 

The protonolysis of alkenyldialkylboranes to give -alkenes can be conducted, in most cases, under neutral conditions using methanol. More hindered alkenyldisiamylboranes react less well, unless a small amount of a carboxylic acid is added. A variety of Z-alkenyl pheromones was prepared using this method. The synthesis of trans-alkenes and unsymmetrical ketones was also accomplished using vinylic organoborane chemistry.7... 

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