58347-22-1

Upstream product

• 55718-76-8 2-chloro-1,3,2-benzodioxaborole 
• 1199-95-7 1-(trimethylstannyl)-2-phenylethyne 
• 1086138-68-2 C₁₀H₇BO₃ 
• 536-74-3 phenylacetylene 

Downstream Products

• 809277-80-3 3-(1,3,2-benzodioxaborolyl)-4-phenyl-1,2-bis(tricarbonylcobalta)tetrahedrane 
• 885333-59-5 closo-1-phenylethynyl-2,3-diethyl-2,3-dicarbaheptaborane⁽⁷⁾ 

Relevant academic research and scientific papers

Boron Recycling in the Metal-Free Transfer C-H Borylation of Terminal Alkynes and Heteroarenes

Transfer C-H borylation is an isodesmic approach to the borylation reaction using B-C-containing molecules as boron sources. In this work, we report that 2-mercaptothiazole and other analogues are active for the metal-free borylation of heterocycles and t

Haloboration of internal alkynes with boronium and borenium cations as a route to tetrasubstituted alkenes

Hail boration! 2-Dimethylaminopyridine-ligated dihaloborocations [X 2B(2-DMAP)]+ with a strained four-membered boracycle were used for the haloboration of terminal and dialkyl internal alkynes (see scheme). Esterification then provided vinyl boronate esters as useful precursors to tetrasubstituted alkenes. Following mechanistic studies, the scope of the haloboration was expanded simply by variation of the amine. Pin=2,3-dimethyl-2, 3-butanedioxy.

Cobalt-mediated cyclooligomerization reactions of borylacetylenes

Reaction of bis(diethylamino) acetylene (1) with lithium and chlorobis(dimethylamino)borane yields 1-[bis(dimethylamino)boryl]-2- (diethylamino)acetylene (2). Treatment of 1-aryl-2-(trimethylstannyl)acetylenes 3 with chlorobis(diisopropylamino)borane results in the quantitative formation of 1-aryl-2-[bis(diisopropylamino)boryl]acetylene compounds 4. The 1-aryl-2-borylacetylene derivatives 5, 6, and 7 are obtained by the reaction of 3 with the appropriate haloborane, or by reacting 4 with two equivalents of HCl and one equivalent of catechol, dithiocatechol and 2-hydroxythiophenol. The catalytic cyclotrimerizations of 5a-d with [CpCo(CO)2] or [Co 2(CO)8] lead to isomeric mixtures of the triborylbenzene derivatives 8a-d and 8a′-d′, whereas 6a-d and 7a-b undergo cyclotrimerization only with catalytic amount of [Co2(CO) 8], to give isomeric mixtures of the triborylbenzene derivatives 12a-d/12a′-d′ and 13a-b/13a′-b′, respectively. The reaction of 2 with a stoichiometric amount of (η5- cyclopentadienyl)bis(ethene)cobalt leads to (η5-cyclopentadienyl) (η4-cyclobutadiene)cobalt complexes 9. The analogous complexes 10 and 11 are obtained by the reactions of 6 and 7 with a stoichiometric amount of (η5-cyclopentadienyl)dicarbonylcobalt. Treatment of Co 2(CO)8 with 5a, 6a, and 7a yields the dicobaltatetrahedranes 14a, 15a and 16a. Compound 15a reacts with two equivalents of diphenylacetylene and 1-(1,3,2-benzodioxaborolyl)-2- phenylacetylene (5a), to furnish (1,3,2-benzodithiaborolyl)pentaphenylbenzene (17) and bis(1,3,2-benzodioxaborolyl)(1,3,2-benzodithiaborolyl)triphenylbenzene (18), respectively. The new compounds have been characterized by NMR spectroscopy and mass spectrometry, as well as by X-ray structural analyses for 4a, 5a, 6a, and 10a. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004.