Literature DB >> 16076182

A reaction for sp(3)-sp(3) C-C bond formation via cooperation of Lewis acid-promoted/Rh-catalyzed C-H bond activation.

Lei Shi1, Yong-Qiang Tu, Min Wang, Fu-Min Zhang, Chun-An Fan, Yu-Ming Zhao, Wu-Jiong Xia.   

Abstract

A new method for intermolecular sp3-sp3 C-C bond formation between primary aliphatic alcohol and olefin by use of a RhCl(PPh3)3 (cat.)/BF3.OEt2 (2.5 equiv)/BuBr (0.5 equiv)/toluene system was first disclosed, which possessed quite significant utilities for organic synthesis, especially for that of secondary alcohols. The most significant aspect is the discovery that rhodium-catalyzed C-H bond activation of alcohols is feasible under Lewis acid-promoted conditions.

Entities:  

Year:  2005        PMID： 16076182     DOI： 10.1021/ja0528331

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


  16 in total

Review 1.  Catalytic carbonyl addition through transfer hydrogenation: a departure from preformed organometallic reagents.

Authors:  John F Bower; In Su Kim; Ryan L Patman; Michael J Krische
Journal:  Angew Chem Int Ed Engl       Date:  2009       Impact factor: 15.336

2.  Carbonyl propargylation from the alcohol or aldehyde oxidation level employing 1,3-enynes as surrogates to preformed allenylmetal reagents: a ruthenium-catalyzed C-C bond-forming transfer hydrogenation.

Authors:  Ryan L Patman; Vanessa M Williams; John F Bower; Michael J Krische
Journal:  Angew Chem Int Ed Engl       Date:  2008       Impact factor: 15.336

Review 3.  Enantioselective iridium-catalyzed carbonyl allylation from the alcohol oxidation level via transfer hydrogenation: minimizing pre-activation for synthetic efficiency.

Authors:  Soo Bong Han; In Su Kim; Michael J Krische
Journal:  Chem Commun (Camb)       Date:  2009-10-16       Impact factor: 6.222

4.  Formation of C-C Bonds via Iridium-Catalyzed Hydrogenation and Transfer Hydrogenation.

Authors:  John F Bower; Michael J Krische
Journal:  Top Organomet Chem       Date:  2011-01-01       Impact factor: 1.311

5.  Direct vinylation of alcohols or aldehydes employing alkynes as vinyl donors: a ruthenium catalyzed C-C bond-forming transfer hydrogenation.

Authors:  Ryan L Patman; Mani Raj Chaulagain; Vanessa M Williams; Michael J Krische
Journal:  J Am Chem Soc       Date:  2009-02-18       Impact factor: 15.419

6.  Pd(OAc)(2)-catalyzed domino reactions of 1,2-dihaloarenes and 2-haloaryl arenesulfonates with Grignard reagents: efficient synthesis of substituted fluorenes.

Authors:  Cheng-Guo Dong; Qiao-Sheng Hu
Journal:  Tetrahedron       Date:  2008-03-10       Impact factor: 2.457

7.  C-H bond functionalization via hydride transfer: Lewis acid catalyzed alkylation reactions by direct intramolecular coupling of sp3 C-H bonds and reactive alkenyl oxocarbenium intermediates.

Authors:  Kevin M McQuaid; Dalibor Sames
Journal:  J Am Chem Soc       Date:  2009-01-21       Impact factor: 15.419

8.  Enantioselective iridium-catalyzed carbonyl allylation from the alcohol or aldehyde oxidation level using allyl acetate as an allyl metal surrogate.

Authors:  In Su Kim; Ming-Yu Ngai; Michael J Krische
Journal:  J Am Chem Soc       Date:  2008-04-29       Impact factor: 15.419

9.  Enantioselective iridium-catalyzed carbonyl allylation from the alcohol or aldehyde oxidation level via transfer hydrogenative coupling of allyl acetate: departure from chirally modified allyl metal reagents in carbonyl addition.

Authors:  In Su Kim; Ming-Yu Ngai; Michael J Krische
Journal:  J Am Chem Soc       Date:  2008-10-08       Impact factor: 15.419

10.  C-H bond functionalization via hydride transfer: synthesis of dihydrobenzopyrans from ortho-vinylaryl akyl ethers.

Authors:  Kevin M McQuaid; Jonathan Z Long; Dalibor Sames
Journal:  Org Lett       Date:  2009-07-16       Impact factor: 6.005
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