Literature DB >> 19663391

Rh-catalyzed reductive coupling reaction of aldehydes with conjugated dienes promoted by triethylborane.

Masanari Kimura1, Daisuke Nojiri, Masahiro Fukushima, Shuichi Oi, Yusuke Sonoda, Yoshio Inoue.   

Abstract

Rh(I) catalyzes the reductive coupling reaction of a wide variety of aldehydes with conjugated dienes in the presence of a stoichiometric amount of triethylborane to provide homoallyl alcohols in a single operation.

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Year:  2009        PMID： 19663391     DOI： 10.1021/ol901527b

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  11 in total

Review 1.  Engaging Aldehydes in CuH-Catalyzed Reductive Coupling Reactions: Stereoselective Allylation with Unactivated 1,3-Diene Pronucleophiles.

Authors:  Chengxi Li; Kwangmin Shin; Richard Y Liu; Stephen L Buchwald
Journal:  Angew Chem Int Ed Engl       Date:  2019-10-22       Impact factor: 15.336

2.  Iridium Catalyzed Hydro-hydroxyalkylation of Butadiene: Carbonyl Crotylation.

Authors:  Jason R Zbieg; Takeo Fukuzumi; Michael J Krische
Journal:  Adv Synth Catal       Date:  2010-10-04       Impact factor: 5.837

3.  Enthalpy vs Entropy Driven Complexation of Homoallylic Alcohols by Rh(I) Complexes.

Authors:  Sung Ok Kang; Vincent M Lynch; Victor W Day; Eric V Anslyn
Journal:  Organometallics       Date:  2011-10-25       Impact factor: 3.876

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

Authors:  Brian J Spinello; Jessica Wu; Yoon Cho; Michael J Krische
Journal:  J Am Chem Soc       Date:  2021-08-20       Impact factor: 16.383

5.  Direct, redox-neutral prenylation and geranylation of secondary carbinol C-H bonds: C4-regioselectivity in ruthenium-catalyzed C-C couplings of dienes to α-hydroxy esters.

Authors:  Joyce C Leung; Laina M Geary; Te-Yu Chen; Jason R Zbieg; Michael J Krische
Journal:  J Am Chem Soc       Date:  2012-09-17       Impact factor: 15.419

6.  Regioselective ruthenium catalyzed hydrohydroxyalkylation of dienes with 3-hydroxy-2-oxindoles: prenylation, geranylation, and beyond.

Authors:  Te-Yu Chen; Michael J Krische
Journal:  Org Lett       Date:  2013-05-30       Impact factor: 6.005

Review 7.  Intermolecular Metal-Catalyzed Reductive Coupling of Dienes, Allenes, and Enynes with Carbonyl Compounds and Imines.

Authors:  Michael Holmes; Leyah A Schwartz; Michael J Krische
Journal:  Chem Rev       Date:  2018-06-13       Impact factor: 60.622

8.  Chain Walking of Allylrhodium Species Towards Esters During Rhodium-Catalyzed Nucleophilic Allylations of Imines.

Authors:  Jose I Martínez; Joshua J Smith; Hamish B Hepburn; Hon Wai Lam
Journal:  Angew Chem Int Ed Engl       Date:  2015-12-03       Impact factor: 15.336

9.  Arylative Intramolecular Allylation of Ketones with 1,3-Enynes Enabled by Catalytic Alkenyl-to-Allyl 1,4-Rhodium(I) Migration.

Authors:  Benjamin M Partridge; Michael Callingham; William Lewis; Hon Wai Lam
Journal:  Angew Chem Int Ed Engl       Date:  2017-05-19       Impact factor: 15.336

Review 10.  Allenes and Dienes as Chiral Allylmetal Pronucleophiles in Catalytic Enantioselective C=X Addition: Historical Perspective and State-of-The-Art Survey.

Authors:  Ming Xiang; Dana E Pfaffinger; Michael J Krische
Journal:  Chemistry       Date:  2021-07-29       Impact factor: 5.020
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