Literature DB >> 30517785

Nickel-Catalyzed Reductive [2+2] Cycloaddition of Alkynes.

Santiago Cañellas1,2, John Montgomery3, Miquel À Pericàs1,4.   

Abstract

The nickel-catalyzed synthesis of tetrasubstituted cyclobutenes from alkynes is reported. This transformation is uniquely promoted by the use of a primary aminophosphine, an unusual ligand in nickel catalysis. Mechanistic insights for this new transformation are provided, and postreaction modifications of the cyclobutene products to stereodefined cyclic and acyclic compounds are reported, including the synthesis of epi-truxillic acid.

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Year:  2018        PMID： 30517785      PMCID： PMC6470007          DOI： 10.1021/jacs.8b09677

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN： 0002-7863            Impact factor:   15.419


  61 in total

1.  Synthesis of cyclopentenols and cyclopentenones via nickel-catalyzed reductive cycloaddition.

Authors:  Aireal D Jenkins; Ananda Herath; Minsoo Song; John Montgomery
Journal:  J Am Chem Soc       Date:  2011-08-18       Impact factor: 15.419

2.  Antinociceptive activities of alpha-truxillic acid and beta-truxinic acid derivatives.

Authors:  Yu-Ming Chi; Motoyuki Nakamura; Xi-Ying Zhao; Toyokichi Yoshizawa; Wen-Mei Yan; Fumio Hashimoto; Junei Kinjo; Toshihiro Nohara; Shinobu Sakurada
Journal:  Biol Pharm Bull       Date:  2006-03       Impact factor: 2.233

3.  Synthesis of cyclobutenes and allenes by cobalt-catalyzed cross-dimerization of simple alkenes with 1,3-enynes.

Authors:  Akira Nishimura; Eri Tamai; Masato Ohashi; Sensuke Ogoshi
Journal:  Chemistry       Date:  2014-04-29       Impact factor: 5.236

4.  Gold(I)-catalyzed intermolecular [2+2] cycloaddition of alkynes with alkenes.

Authors:  Verónica López-Carrillo; Antonio M Echavarren
Journal:  J Am Chem Soc       Date:  2010-07-14       Impact factor: 15.419

5.  Stable, Well-Defined Nickel(0) Catalysts for Catalytic C-C and C-N Bond Formation.

Authors:  Alex J Nett; Santiago Cañellas; Yuki Higuchi; Michael T Robo; Jeanne M Kochkodan; M Taylor Haynes; Jeff W Kampf; John Montgomery
Journal:  ACS Catal       Date:  2018-06-11       Impact factor: 13.084

6.  Transition-metal-catalyzed reactions involving imidazolium salt/N-heterocyclic carbene couples as substrates.

Authors:  Nicolas D Clement; Kingsley J Cavell
Journal:  Angew Chem Int Ed Engl       Date:  2004-07-19       Impact factor: 15.336

Review 7.  Nickel-catalyzed reductive cyclizations and couplings.

Authors:  John Montgomery
Journal:  Angew Chem Int Ed Engl       Date:  2004-07-26       Impact factor: 15.336

8.  Nickel-catalyzed intermolecular [2 + 2] cycloaddition of conjugated enynes with alkenes.

Authors:  Akira Nishimura; Masato Ohashi; Sensuke Ogoshi
Journal:  J Am Chem Soc       Date:  2012-09-14       Impact factor: 15.419

9.  Noninnocent behavior of ancillary ligands: apparent trans coupling of a saturated N-heterocyclic carbene unit with an ethyl ligand mediated by nickel.

Authors:  Tobias Steinke; Bryan K Shaw; Howard Jong; Brian O Patrick; Michael D Fryzuk; Jennifer C Green
Journal:  J Am Chem Soc       Date:  2009-08-05       Impact factor: 15.419

10.  Reductive Cyclopropanations Catalyzed by Dinuclear Nickel Complexes.

Authors:  You-Yun Zhou; Christopher Uyeda
Journal:  Angew Chem Int Ed Engl       Date:  2016-01-28       Impact factor: 15.336
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  3 in total

1.  Catalytic Enantioselective Synthesis of Cyclobutenes from Alkynes and Alkenyl Derivatives.

Authors:  Mahesh M Parsutkar; Vinayak Vishnu Pagar; T V RajanBabu
Journal:  J Am Chem Soc       Date:  2019-09-12       Impact factor: 15.419

2.  Iron-Catalyzed Vinylsilane Dimerization and Cross-Cycloadditions with 1,3-Dienes: Probing the Origins of Chemo- and Regioselectivity.

Authors:  C Rose Kennedy; Matthew V Joannou; Janelle E Steves; Jordan M Hoyt; Carli B Kovel; Paul J Chirik
Journal:  ACS Catal       Date:  2021-01-13       Impact factor: 13.084

3.  Allylic alcohol synthesis by Ni-catalyzed direct and selective coupling of alkynes and methanol.

Authors:  Herong Chen; Zhijun Zhou; Wangqing Kong
Journal:  Chem Sci       Date:  2021-06-07       Impact factor: 9.825
  3 in total

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