Literature DB >> 34415159

Conversion of Primary Alcohols and Butadiene to Branched Ketones via Merged Transfer Hydrogenative Carbonyl Addition-Redox Isomerization Catalyzed by Rhodium.

Brian J Spinello1, Jessica Wu1, Yoon Cho1, Michael J Krische1.   

Abstract

The first examples of rhodium-catalyzed carbonyl addition via hydrogen autotransfer are described, as illustrated in tandem butadiene-mediated carbonyl addition-redox isomerizations that directly convert primary alcohols to isobutyl ketones. Related reductive coupling-redox isomerizations of aldehyde reactants mediated by sodium formate also are reported. A double-labeling crossover experiment reveals that the rhodium alkoxide obtained upon carbonyl addition enacts redox isomerization without dissociation of rhodium at any intervening stage.

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Year:  2021        PMID： 34415159      PMCID： PMC8739284          DOI： 10.1021/jacs.1c07230

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN： 0002-7863            Impact factor:   16.383


  55 in total

1.  Transposition of allylic alcohols into carbonyl compounds mediated by transition metal complexes.

Authors:  Ramalinga Uma; Christophe Crévisy; René Grée
Journal:  Chem Rev       Date:  2003-01       Impact factor: 60.622

2.  Enantioselective C-H crotylation of primary alcohols via hydrohydroxyalkylation of butadiene.

Authors:  Jason R Zbieg; Eiji Yamaguchi; Emma L McInturff; Michael J Krische
Journal:  Science       Date:  2012-03-22       Impact factor: 47.728

3.  Direct Aldehyde C-H Arylation and Alkylation via the Combination of Nickel, Hydrogen Atom Transfer, and Photoredox Catalysis.

Authors:  Xiaheng Zhang; David W C MacMillan
Journal:  J Am Chem Soc       Date:  2017-08-14       Impact factor: 15.419

4.  CuH-Catalyzed Enantioselective Ketone Allylation with 1,3-Dienes: Scope, Mechanism, and Applications.

Authors:  Chengxi Li; Richard Y Liu; Luke T Jesikiewicz; Yang Yang; Peng Liu; Stephen L Buchwald
Journal:  J Am Chem Soc       Date:  2019-03-12       Impact factor: 15.419

5.  Transition metal-catalyzed alkene isomerization as an enabling technology in tandem, sequential and domino processes.

Authors:  Daniele Fiorito; Simone Scaringi; Clément Mazet
Journal:  Chem Soc Rev       Date:  2020-12-09       Impact factor: 54.564

Review 6.  Nickel-catalyzed reductive cyclizations and couplings.

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

7.  Enantioselective reductive coupling of acetylene to N-arylsulfonyl imines via rhodium catalyzed C-C bond-forming hydrogenation: (Z)-dienyl allylic amines.

Authors:  Eduardas Skucas; Jong Rock Kong; Michael J Krische
Journal:  J Am Chem Soc       Date:  2007-05-19       Impact factor: 15.419

8.  Cobalt-Catalysed Asymmetric Hydrovinylation of 1,3-Dienes.

Authors:  Yam N Timsina; Rakesh K Sharma; T V RajanBabu
Journal:  Chem Sci       Date:  2015-04-23       Impact factor: 9.825

9.  From Hydrogenation to Transfer Hydrogenation to Hydrogen Auto-Transfer in Enantioselective Metal-Catalyzed Carbonyl Reductive Coupling: Past, Present, and Future.

Authors:  Catherine Gazolla Santana; Michael J Krische
Journal:  ACS Catal       Date:  2021-04-22       Impact factor: 13.084

10.  Control of Absolute Stereochemistry in Transition-Metal-Catalyzed Hydrogen Borrowing Reactions.

Authors:  Timothy Kwok; Oskar Hoff; Roly J Armstrong; Timothy James Donohoe
Journal:  Chemistry       Date:  2020-04-16       Impact factor: 5.236
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