Literature DB >> 32431470

Synthesis of Unsaturated Silyl Heterocycles via an Intramolecular Silyl-Heck Reaction.

William B Reid1, Jesse R McAtee1, Donald A Watson1.   

Abstract

We report the synthesis of unsaturated silacycles via an intramolecular silyl-Heck reaction. Using palladium catalysis, silicon electrophiles tethered to alkenes cyclize to form 5- and 6-membered silicon heterocycles. The effects of alkene substitution and tether length on the efficiency and regioselectivity of the cyclizations are described. Finally, through the use of an intramolecular tether, the first examples of disubstituted alkenes in silyl-Heck reactions are reported.

Entities:  

Year:  2019        PMID： 32431470      PMCID： PMC7236810          DOI： 10.1021/acs.organomet.9b00498

Source DB:  PubMed          Journal:  Organometallics        ISSN： 0276-7333            Impact factor:   3.876


  33 in total

1.  Optimization of 3-(1H-indazol-3-ylmethyl)-1,5-benzodiazepines as potent, orally active CCK-A agonists.

Authors:  B R Henke; C J Aquino; L S Birkemo; D K Croom; R W Dougherty; G N Ervin; M K Grizzle; G C Hirst; M K James; M F Johnson; K L Queen; R G Sherrill; E E Sugg; E M Suh; J W Szewczyk; R J Unwalla; J Yingling; T M Willson
Journal:  J Med Chem       Date:  1997-08-15       Impact factor: 7.446

Review 2.  Synthesis of heterocycles via palladium-catalyzed oxidative addition.

Authors:  Gilson Zeni; Richard C Larock
Journal:  Chem Rev       Date:  2006-11       Impact factor: 60.622

3.  Preparation of allyl and vinyl silanes by the palladium-catalyzed silylation of terminal olefins: a silyl-Heck reaction.

Authors:  Jesse R McAtee; Sara E S Martin; Derek T Ahneman; Keywan A Johnson; Donald A Watson
Journal:  Angew Chem Int Ed Engl       Date:  2012-03-01       Impact factor: 15.336

4.  Simplified Preparation of Trialkylvinylsilanes via the Silyl-Heck Reaction Utilizing a Second Generation Catalyst.

Authors:  Jesse R McAtee; Sarah B Krause; Donald A Watson
Journal:  Adv Synth Catal       Date:  2015-07-14       Impact factor: 5.837

5.  Silylenes, silenes, and disilenes: novel silicon-based reagents for organic synthesis?

Authors:  Henrik Ottosson; Patrick G Steel
Journal:  Chemistry       Date:  2006-02-08       Impact factor: 5.236

6.  Synthesis of various silacycles via the lewis acid-catalyzed intramolecular trans-hydrosilylation of unactivated alkynes

Authors: 
Journal:  J Org Chem       Date:  2000-12-29       Impact factor: 4.354

7.  Immobilized alpha-diazophosphonoacetate as a versatile key precursor for palladium catalyzed indole synthesis on a polymer support.

Authors:  Kazuo Yamazaki; Yoshinori Kondo
Journal:  Chem Commun (Camb)       Date:  2002-02-07       Impact factor: 6.222

8.  Functionalized cyclobutanes via Heck cyclization.

Authors:  Anna Innitzer; Lothar Brecker; Johann Mulzer
Journal:  Org Lett       Date:  2007-09-27       Impact factor: 6.005

9.  The First Example of Nickel-Catalyzed Silyl-Heck Reactions: Direct Activation of Silyl Triflates Without Iodide Additives.

Authors:  Jesse R McAtee; Sara E S Martin; Andrew P Cinderella; William B Reid; Keywan A Johnson; Donald A Watson
Journal:  Tetrahedron       Date:  2014-07-08       Impact factor: 2.457

10.  Direct Silyl-Heck Reaction of Chlorosilanes.

Authors:  Kazuhiro Matsumoto; Jiadi Huang; Yuki Naganawa; Haiqing Guo; Teruo Beppu; Kazuhiko Sato; Shigeru Shimada; Yumiko Nakajima
Journal:  Org Lett       Date:  2018-04-04       Impact factor: 6.005
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