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The Et3B-initiated reaction of gamma-unsubstituted propargyl alcohols with dibutylchlorostannane (Bu2SnClH) at low temperature gave (Z)-vinylstannanes with high regio- and stereoselectivity. The corresponding alkyl propargyl ethers also underwent regio- and stereoselective homolytic hydrostannylation with Bu2SnClH; however, the regioselectivity was not so high as that with the propargyl alcohols.
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http://dx.doi.org/10.1021/jo035012s | DOI Listing |
Org Biomol Chem
August 2025
Faculty of Chemical Engineering and Energy Technology, Shanghai Institute of Technology, 100 Haiquan Road, Shanghai 201418, P. R. China.
The cascade reaction of -aminophenyl/-hydroxyphenyl propargyl alcohols with β-sulfinyl esters was explored under basic conditions. -Aminophenyl propargyl alcohols were converted into 3-sulfinyl indoles using KOH, while 3-sulfonyl indoles were obtained using CsCO and CuI. -Hydroxyphenyl propargyl alcohols were only compatible with the sulfonylation process using CsCO and CuI, delivering 3-sulfonyl benzofurans.
View Article and Find Full Text PDFJ Org Chem
August 2025
CNRS, Institut des Sciences Chimiques de Rennes (ISCR), University of Rennes, UMR 6226, F-35000 Rennes, France.
Herein, a novel synthesis of different indolopyrido-quinazolinones by the reaction of easily accessible 2-indolyl quinazolinone with propargylic alcohols has been developed. This [4 + 2] annulation proceeds through sequential acid-catalyzed C-propargylation and base-promoted -annulation by forming C-C and C-N bonds in a one-pot operation. Interestingly, the reagent-controlled regiodivergent annulations were observed leading to diversely fused N1-C2 or C2-N3 indolopyrido-quinazolinones.
View Article and Find Full Text PDFOrg Lett
August 2025
Center for Supramolecular Chemistry and Catalysis and Department of Chemistry, College of Sciences, Shanghai University, Shanghai 200444, China.
We present an asymmetric propargylic substitution reaction of -hydroxy aryl ketones with propargylic acetates catalyzed by a B/Cu system. The reaction initiates with the activation of -hydroxy aryl ketones via achiral borinic acid to form a tetracoordinated enol boronate complex, which then reacts with propargylic acetates catalyzed by copper salts with chiral P,N,N-ligand. This method is amenable to a broad range of substrates and delivers a series of chiral β-ethynyl ketones with high yields and remarkable enantioselectivity under mild conditions.
View Article and Find Full Text PDFJ Am Chem Soc
August 2025
Department of Chemistry and Biochemistry, University of California, Santa Barbara, California 93117, United States.
Despite successes in achieving asymmetric induction in enyne cycloisomerization, few systems are applicable to each of the typical 6-, 5-, and 5- cyclization/cycloisomerization modes. By appending a synthetically valuable hydroxymethyl group at the alkyne end, a hydrogen bond between the HO group of the propargyl alcohol moiety and a chiral ligand basic group offers a novel asymmetric induction strategy in gold-catalyzed enyne cycloisomerization reactions. Both 1,5-enynes and 1,6-enynes are suitable substrates, and 5-, 5-, and 6- cyclizations lead to outstanding enantioselectivities.
View Article and Find Full Text PDFACS Catal
July 2025
Department of Chemistry, University of Minnesota, 207 Pleasant St., SE, Minneapolis, Minnesota 55455.
We have established an ambient temperature, one-pot, acid-catalyzed, three-component process involving in situ formation of a tetrayne or triyne that spontaneously cyclizes to a benzyne intermediate. This is rapidly captured to give a diverse range of polycyclic phthalan derivatives. Product structural diversity was enhanced by employing various combinations of alkyne substrates and benzyne trapping reagents.
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