Literature DB >> 19894699

Boc groups as protectors and directors for Ir-catalyzed C-H borylation of heterocycles.

Venkata A Kallepalli1, Feng Shi, Sulagna Paul, Edith N Onyeozili, Robert E Maleczka, Milton R Smith.   

Abstract

Ir-catalyzed C-H borylation is found to be compatible with Boc protecting groups. Thus, pyrroles, indoles, and azaindoles can be selectively functionalized at C-H positions beta to N. The Boc group can be removed on thermolysis or left intact during subsequent transformations.

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Year:  2009        PMID： 19894699      PMCID： PMC3876461          DOI： 10.1021/jo901822b

Source DB:  PubMed          Journal:  J Org Chem        ISSN： 0022-3263            Impact factor:   4.354


  9 in total

1.  A stoichiometric aromatic CbondH borylation catalyzed by iridium(i)/2,2'-bipyridine complexes at room temperature.

Authors:  Tatsuo Ishiyama; Jun Takagi; John F Hartwig; Norio Miyaura
Journal:  Angew Chem Int Ed Engl       Date:  2002-08-16       Impact factor: 15.336

2.  Ir-catalyzed borylation of C-H bonds in N-containing heterocycles: regioselectivity in the synthesis of heteroaryl boronate esters.

Authors:  Ibraheem A I Mkhalid; David N Coventry; David Albesa-Jove; Andrei S Batsanov; Judith A K Howard; Robin N Perutz; Todd B Marder
Journal:  Angew Chem Int Ed Engl       Date:  2006-01-09       Impact factor: 15.336

3.  Synthesis of rhazinicine by a metal-catalyzed C-H bond functionalization strategy.

Authors:  Elizabeth M Beck; Richard Hatley; Matthew J Gaunt
Journal:  Angew Chem Int Ed Engl       Date:  2008       Impact factor: 15.336

4.  Microwave-accelerated iridium-catalyzed borylation of aromatic C-H bonds.

Authors:  Peter Harrisson; James Morris; Todd B Marder; Patrick G Steel
Journal:  Org Lett       Date:  2009-08-20       Impact factor: 6.005

5.  Remarkably selective iridium catalysts for the elaboration of aromatic C-H bonds.

Authors:  Jian-Yang Cho; Man Kin Tse; Daniel Holmes; Robert E Maleczka; Milton R Smith
Journal:  Science       Date:  2001-11-22       Impact factor: 47.728

6.  Regioselective aromatic borylation in an inert solvent.

Authors:  M K Tse; J Y Cho; M R Smith
Journal:  Org Lett       Date:  2001-09-06       Impact factor: 6.005

7.  Highly efficient monophosphine-based catalyst for the palladium-catalyzed suzuki-miyaura reaction of heteroaryl halides and heteroaryl boronic acids and esters.

Authors:  Kelvin Billingsley; Stephen L Buchwald
Journal:  J Am Chem Soc       Date:  2007-02-28       Impact factor: 15.419

8.  Enantioselective synthesis of SM-130686 based on the development of asymmetric Cu(I)F catalysis to access 2-oxindoles containing a tetrasubstituted carbon.

Authors:  Daisuke Tomita; Kenzo Yamatsugu; Motomu Kanai; Masakatsu Shibasaki
Journal:  J Am Chem Soc       Date:  2009-05-27       Impact factor: 15.419

9.  C-H activation/borylation/oxidation: a one-pot unified route to meta-substituted phenols bearing ortho-/para-directing groups.

Authors:  Robert E Maleczka; Feng Shi; Daniel Holmes; Milton R Smith
Journal:  J Am Chem Soc       Date:  2003-07-02       Impact factor: 15.419
  9 in total
  22 in total

1.  Synthesis of 2-D-L-Tryptophan by Sequential Ir-Catalyzed Reactions.

Authors:  Ravikrishna Vallakati; Abel T Plotnikov; Ryan A Altman
Journal:  Tetrahedron       Date:  2019-02-26       Impact factor: 2.457

2.  Outer-sphere direction in iridium C-H borylation.

Authors:  Philipp C Roosen; Venkata A Kallepalli; Buddhadeb Chattopadhyay; Daniel A Singleton; Robert E Maleczka; Milton R Smith
Journal:  J Am Chem Soc       Date:  2012-07-03       Impact factor: 15.419

3.  11-Step Total Synthesis of Teleocidins B-1-B-4.

Authors:  Hugh Nakamura; Kosuke Yasui; Yuzuru Kanda; Phil S Baran
Journal:  J Am Chem Soc       Date:  2019-01-15       Impact factor: 15.419

4.  Total Synthesis of Verruculogen and Fumitremorgin A Enabled by Ligand-Controlled C-H Borylation.

Authors:  Yu Feng; Dane Holte; Jochen Zoller; Shigenobu Umemiya; Leah R Simke; Phil S Baran
Journal:  J Am Chem Soc       Date:  2015-08-11       Impact factor: 15.419

5.  Harnessing C-H Borylation/Deborylation for Selective Deuteration, Synthesis of Boronate Esters, and Late Stage Functionalization.

Authors:  Venkata A Kallepalli; Kristin A Gore; Feng Shi; Luis Sanchez; Ghayoor A Chotana; Susanne L Miller; Robert E Maleczka; Milton R Smith
Journal:  J Org Chem       Date:  2015-08-07       Impact factor: 4.354

6.  Bismuth Acetate as a Catalyst for the Sequential Protodeboronation of Di- and Triborylated Indoles.

Authors:  Fangyi Shen; Sriram Tyagarajan; Damith Perera; Shane W Krska; Peter E Maligres; Milton R Smith; Robert E Maleczka
Journal:  Org Lett       Date:  2016-03-21       Impact factor: 6.005

7.  Total Synthesis of Tambromycin Enabled by Indole C-H Functionalization.

Authors:  Galen P Miley; Jennifer C Rote; Richard B Silverman; Neil L Kelleher; Regan J Thomson
Journal:  Org Lett       Date:  2018-03-27       Impact factor: 6.005

8.  Evolution of C-H Bond Functionalization from Methane to Methodology.

Authors:  John F Hartwig
Journal:  J Am Chem Soc       Date:  2015-12-15       Impact factor: 15.419

9.  A traceless directing group for C-H borylation.

Authors:  Sean M Preshlock; Donald L Plattner; Peter E Maligres; Shane W Krska; Robert E Maleczka; Milton R Smith
Journal:  Angew Chem Int Ed Engl       Date:  2013-11-12       Impact factor: 15.336

10.  Enantioselective Synthesis of (-)-Vallesine: Late-Stage C17-Oxidation via Complex Indole Boronation.

Authors:  Alyssa H Antropow; Nicholas R Garcia; Kolby L White; Mohammad Movassaghi
Journal:  Org Lett       Date:  2018-06-04       Impact factor: 6.005
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