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Rh(I)-catalyzed CO gas-free carbonylative cyclization reactions of alkynes with 2-bromophenylboronic acids using formaldehyde.
Org Lett. 2009 Apr 16; 11(8):1777-80.OL

Abstract

The rhodium(I)-catalyzed reaction of alkynes with 2-bromophenylboronic acids in the presence of paraformaldehyde resulted in a CO gas-free carbonylative cyclization, yielding indenone derivatives. [RhCl(BINAP)](2) and [RhCl(cod)](2) were responsible for the decarbonylation of formaldehyde and the subsequent carbonylation of alkynes with 2-haloboronic acids, respectively, leading to efficient whole carbonylation. Sterically bulky and electron-withdrawing groups on unsymmetrically substituted alkynes favored the alpha-position of indenones.

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Authors+Show Affiliations

Morimoto T
Graduate School of Materials Science, Nara Institute of Science and Technology (NAIST), Takayama, Ikoma, Nara 630-0192, Japan.
Yamasaki K
No affiliation info available
Hirano A
No affiliation info available
Tsutsumi K
No affiliation info available
Kagawa N
No affiliation info available
Kakiuchi K
No affiliation info available
Harada Y
No affiliation info available
Fukumoto Y
No affiliation info available
Chatani N
No affiliation info available
Nishioka T
No affiliation info available

Pub Type(s)

Journal Article

Language

eng

PubMed ID

19301863

Citation

Morimoto, Tsumoru, et al. "Rh(I)-catalyzed CO Gas-free Carbonylative Cyclization Reactions of Alkynes With 2-bromophenylboronic Acids Using Formaldehyde." Organic Letters, vol. 11, no. 8, 2009, pp. 1777-80.
Morimoto T, Yamasaki K, Hirano A, et al. Rh(I)-catalyzed CO gas-free carbonylative cyclization reactions of alkynes with 2-bromophenylboronic acids using formaldehyde. Org Lett. 2009;11(8):1777-80.
Morimoto, T., Yamasaki, K., Hirano, A., Tsutsumi, K., Kagawa, N., Kakiuchi, K., Harada, Y., Fukumoto, Y., Chatani, N., & Nishioka, T. (2009). Rh(I)-catalyzed CO gas-free carbonylative cyclization reactions of alkynes with 2-bromophenylboronic acids using formaldehyde. Organic Letters, 11(8), 1777-80. https://doi.org/10.1021/ol900327x
Morimoto T, et al. Rh(I)-catalyzed CO Gas-free Carbonylative Cyclization Reactions of Alkynes With 2-bromophenylboronic Acids Using Formaldehyde. Org Lett. 2009 Apr 16;11(8):1777-80. PubMed PMID: 19301863.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Rh(I)-catalyzed CO gas-free carbonylative cyclization reactions of alkynes with 2-bromophenylboronic acids using formaldehyde. AU - Morimoto,Tsumoru, AU - Yamasaki,Kae, AU - Hirano,Akihisa, AU - Tsutsumi,Ken, AU - Kagawa,Natsuko, AU - Kakiuchi,Kiyomi, AU - Harada,Yasuyuki, AU - Fukumoto,Yoshiya, AU - Chatani,Naoto, AU - Nishioka,Takanori, PY - 2009/3/24/entrez PY - 2009/3/24/pubmed PY - 2009/3/24/medline SP - 1777 EP - 80 JF - Organic letters JO - Org Lett VL - 11 IS - 8 N2 - The rhodium(I)-catalyzed reaction of alkynes with 2-bromophenylboronic acids in the presence of paraformaldehyde resulted in a CO gas-free carbonylative cyclization, yielding indenone derivatives. [RhCl(BINAP)](2) and [RhCl(cod)](2) were responsible for the decarbonylation of formaldehyde and the subsequent carbonylation of alkynes with 2-haloboronic acids, respectively, leading to efficient whole carbonylation. Sterically bulky and electron-withdrawing groups on unsymmetrically substituted alkynes favored the alpha-position of indenones. SN - 1523-7052 UR - https://www.unboundmedicine.com/medline/citation/19301863/Rh_I__catalyzed_CO_gas_free_carbonylative_cyclization_reactions_of_alkynes_with_2_bromophenylboronic_acids_using_formaldehyde_ L2 - https://doi.org/10.1021/ol900327x DB - PRIME DP - Unbound Medicine ER -