Literature DB >> 10602204

Nickel(0)-Catalyzed Three-Component Connection Reaction of Dimethylzinc, 1,3-Dienes, and Carbonyl Compounds.

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Abstract

Linear 1:1:1 coupling of dimethylzinc, 1,3-dienes, and carbonyl compounds in this order is facilitated by catalytic amounts of [Ni(acac)(2)] to give (E)-3-hexen-1-ols in good yields under mild conditions [Eq. (a)]. Increasing steric hindrance at the carbonyl group favors formation of the 1:2:1 adduct, and this is the sole product when the carbonyl compound is acetone. acac=acetylacetonate.

Entities:  

Year:  1999        PMID: 10602204     DOI: 10.1002/(sici)1521-3773(19991115)38:22<3386::aid-anie3386>3.0.co;2-w

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN: 1433-7851            Impact factor:   15.336


  5 in total

1.  Stereoselective borylative ketone-diene coupling.

Authors:  Hee Yeon Cho; Zhiyong Yu; James P Morken
Journal:  Org Lett       Date:  2011-09-12       Impact factor: 6.005

2.  Nickel-Catalyzed Enantioselective Coupling of Aldehydes and Electron-Deficient 1,3-Dienes Following an Inverse Regiochemical Course.

Authors:  Thomas Q Davies; Jae Yeon Kim; Alois Fürstner
Journal:  J Am Chem Soc       Date:  2022-10-04       Impact factor: 16.383

3.  Nickel-catalyzed cycloaddition of 1,3-dienes with 3-azetidinones and 3-oxetanones.

Authors:  Ashish Thakur; Megan E Facer; Janis Louie
Journal:  Angew Chem Int Ed Engl       Date:  2013-09-23       Impact factor: 15.336

4.  α-Silicon effect assisted Curtin-Hammett allylation using allylcopper reagents derived from 1,3-dienylsilanes.

Authors:  Shang Gao; Ming Chen
Journal:  Chem Sci       Date:  2019-06-28       Impact factor: 9.825

5.  Nickel-catalyzed coupling reaction of alkyl halides with aryl Grignard reagents in the presence of 1,3-butadiene: mechanistic studies of four-component coupling and competing cross-coupling reactions.

Authors:  Takanori Iwasaki; Asuka Fukuoka; Wataru Yokoyama; Xin Min; Ichiro Hisaki; Tao Yang; Masahiro Ehara; Hitoshi Kuniyasu; Nobuaki Kambe
Journal:  Chem Sci       Date:  2018-01-05       Impact factor: 9.825

  5 in total

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