4-OC-0810-52_1 - ORIGINAL ARTICLE Org. Commun. 2:2 (2009)...

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ORIGINAL ARTICLE The article was published by Academy of Chemistry of Globe Publications www.acgpubs.org/OC/index.htm © Published 05/25/2009 EISSN:1307-6175 Org. Commun . 2:2 (2009) 28-33 Iodine catalyzed and tertiary butyl ammonium bromide promoted preparation of benzoxazaphosphininyl phenylboronates K. R. Kishore K. Reddy, C. Bhupendra Reddy, K. Suresh Kumar, C. Naga Raju and C. Suresh Reddy * Department of Chemistry, Sri Venkateswara University, Tirupati, 517 502, India (Received October 19, 2008; Revised March 14, 2009; Accepted April 15 ,2009) Abstract: Benzoxazaphosphininyl Phenylboronates were prepared by O -Phosphorylation of potassium salt of phenylboronic acid with cyclic phosphoromonochloridates in the presence of stoichiometric amount of Iodine and catalytic amount of tertiary butyl ammonium bromide at 50-60 °C in dry toluene. Keywords : Phosphaphenylboronates; O -Phosphorylation; iodine; tertiary butyl ammonium bromide. 1. Introduction Organoboron compounds were found to possess tremendous utility in organic synthesis. Boronic acids have a leading role in the synthesis 1,2 of organic molecules, analytical chemistry 3,4 and in biological systems as catalysts. 5,6 The discovery of new chemistry involved in Suzuki-Miyaura cross- coupling reaction combined with readily accessibility and ease of handling of products and reagents have established boronic acids and boronates as very useful intermediates in general organic synthesis. 2 Moreover, because of low toxicity and degradation in the environment to friendly boric acid, the organoboronates are regarded as “green compounds”. 2 Organophosphorus compounds such as Phosphoramides are important class of alkylating antitumor agents with activity against a broad spectrum of human cancers including slow-growing solid tumors. 7,8 The field so potential that facture research in it may lead to the discovery of potential drug activity against different bacterial and viral dieses manifestations. Organophosphorus compounds also constitute a family of promising flame retardants due to their unique combustion inhibition properties 9,10 They have been known to act in both gas phase and condensed phase and possibly * Corresponding author: E-mail csrsvu@gmail.com
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Iodine catalyzed preparation of benzoxazaphosphininyl phenylboronates 29 concurrently in both phases 11,12 Synthesis of flame retardants with low flammability and melt dripping limits is in urgent need now-a-days and is gaining much attention. 13 The idea that compounds embedded with organoboron/phosphorus structural features may have interesting properties led to the synthesis of several new organo phosphaboron esters by simple route through the reaction of phosphorochloridates with PhB(OK) 2 in presence of tertiary butyl ammonium bromide (TBAB). 14
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4-OC-0810-52_1 - ORIGINAL ARTICLE Org. Commun. 2:2 (2009)...

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