Literature DB >> 23461762

NHC-Cu-catalyzed protoboration of monosubstituted allenes. Ligand-controlled site selectivity, application to synthesis and mechanism.

Fanke Meng1, Byunghyuck Jung, Fredrik Haeffner, Amir H Hoveyda.   

Abstract

Two types of NHC-Cu complexes catalyze protoborations of terminal allenes to afford valuable 1,1- or trisubstituted vinylboron species with high site selectivity and stereoselectivity. The scope of the method, application to natural product synthesis, and mechanistic basis for the observed selectivity trends are presented.

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Year:  2013        PMID: 23461762      PMCID: PMC3625862          DOI: 10.1021/ol4004178

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


  12 in total

1.  Copper-catalyzed highly regio- and stereoselective directed hydroboration of unsymmetrical internal alkynes: controlling regioselectivity by choice of catalytic species.

Authors:  Kazuhiko Semba; Tetsuaki Fujihara; Jun Terao; Yasushi Tsuji
Journal:  Chemistry       Date:  2012-03-02       Impact factor: 5.236

2.  Elansolid A, a unique macrolide antibiotic from Chitinophaga sancti isolated as two stable atropisomers.

Authors:  Heinrich Steinmetz; Klaus Gerth; Rolf Jansen; Nadin Schläger; Richard Dehn; Silke Reinecke; Andreas Kirschning; Rolf Müller
Journal:  Angew Chem Int Ed Engl       Date:  2011-01-10       Impact factor: 15.336

3.  Bis(allyl)zinc revisited: sigma versus pi bonding of allyl coordination.

Authors:  Crispin Lichtenberg; Julien Engel; Thomas P Spaniol; Ulli Englert; Gerhard Raabe; Jun Okuda
Journal:  J Am Chem Soc       Date:  2012-05-30       Impact factor: 15.419

4.  Organotrifluoroborates: protected boronic acids that expand the versatility of the Suzuki coupling reaction.

Authors:  Gary A Molander; Noel Ellis
Journal:  Acc Chem Res       Date:  2007-01-26       Impact factor: 22.384

5.  Devising boron reagents for orthogonal functionalization through Suzuki-Miyaura cross-coupling.

Authors:  Mamoru Tobisu; Naoto Chatani
Journal:  Angew Chem Int Ed Engl       Date:  2009       Impact factor: 15.336

6.  Site- and enantioselective formation of allene-bearing tertiary or quaternary carbon stereogenic centers through NHC-Cu-catalyzed allylic substitution.

Authors:  Byunghyuck Jung; Amir H Hoveyda
Journal:  J Am Chem Soc       Date:  2012-01-03       Impact factor: 15.419

7.  Regiocontrolled Cu(I)-catalyzed borylation of propargylic-functionalized internal alkynes.

Authors:  Abraham L Moure; Ramón Gómez Arrayás; Diego J Cárdenas; Inés Alonso; Juan C Carretero
Journal:  J Am Chem Soc       Date:  2012-04-18       Impact factor: 15.419

8.  Bis(imidazoline-2-thione)-copper(I) catalyzed regioselective boron addition to internal alkynes.

Authors:  Hye Ryung Kim; Il Gu Jung; Kihyun Yoo; Kwonho Jang; Eun Sun Lee; Jaesook Yun; Seung Uk Son
Journal:  Chem Commun (Camb)       Date:  2009-11-30       Impact factor: 6.222

9.  Palladium-catalyzed cross-coupling reaction of bis(pinacolato)diboron with 1-alkenyl halides or triflates: convenient synthesis of unsymmetrical 1,3-dienes via the borylation-coupling sequence.

Authors:  Jun Takagi; Kou Takahashi; Tatsuo Ishiyama; Norio Miyaura
Journal:  J Am Chem Soc       Date:  2002-07-10       Impact factor: 15.419

10.  Regioselective catalytic hydroboration of propargylic species using Cu(I)-NHC complexes.

Authors:  Jin Kyoon Park; Brian A Ondrusek; D Tyler McQuade
Journal:  Org Lett       Date:  2012-09-04       Impact factor: 6.005

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  20 in total

1.  Catalytic Enantioselective Conjugate Additions of (pin)B-Substituted Allylcopper Compounds Generated in situ from Butadiene or Isoprene.

Authors:  Xiben Li; Fanke Meng; Sebastian Torker; Ying Shi; Amir H Hoveyda
Journal:  Angew Chem Int Ed Engl       Date:  2016-07-20       Impact factor: 15.336

2.  Enantioselective synthesis of boron-substituted quaternary carbon stereogenic centers through NHC-catalyzed conjugate additions of (pinacolato)boron units to enones.

Authors:  Suttipol Radomkit; Amir H Hoveyda
Journal:  Angew Chem Int Ed Engl       Date:  2014-02-24       Impact factor: 15.336

3.  Synthesis of vinyl boronates from aldehydes by a practical boron-Wittig reaction.

Authors:  John R Coombs; Liang Zhang; James P Morken
Journal:  Org Lett       Date:  2015-03-23       Impact factor: 6.005

4.  Generation of α-Boryl Radicals by H. Transfer and their Use in Cycloisomerizations.

Authors:  Shicheng Shi; Farbod Salahi; Hunter B Vibbert; Maleeha Rahman; Scott A Snyder; Jack R Norton
Journal:  Angew Chem Int Ed Engl       Date:  2021-09-15       Impact factor: 16.823

5.  Ligand-Controlled Regioselective Copper-Catalyzed Trifluoromethylation To Generate (Trifluoromethyl)allenes.

Authors:  Brett R Ambler; Santosh Peddi; Ryan A Altman
Journal:  Org Lett       Date:  2015-04-24       Impact factor: 6.005

6.  Catalytic enantioselective protoboration of disubstituted allenes. Access to alkenylboron compounds in high enantiomeric purity.

Authors:  Hwanjong Jang; Byunghyuck Jung; Amir H Hoveyda
Journal:  Org Lett       Date:  2014-08-25       Impact factor: 6.005

7.  Multifunctional organoboron compounds for scalable natural product synthesis.

Authors:  Fanke Meng; Kevin P McGrath; Amir H Hoveyda
Journal:  Nature       Date:  2014-09-18       Impact factor: 49.962

8.  NHC-Cu-catalyzed addition of propargylboron reagents to phosphinoylimines. Enantioselective synthesis of trimethylsilyl-substituted homoallenylamides and application to the synthesis of S-(-)-cyclooroidin.

Authors:  Nicholas W Mszar; Fredrik Haeffner; Amir H Hoveyda
Journal:  J Am Chem Soc       Date:  2014-02-20       Impact factor: 15.419

9.  An efficient, practical, and enantioselective method for synthesis of homoallenylamides catalyzed by an aminoalcohol-derived, boron-based catalyst.

Authors:  Hao Wu; Fredrik Haeffner; Amir H Hoveyda
Journal:  J Am Chem Soc       Date:  2014-03-03       Impact factor: 15.419

10.  A broadly applicable NHC-Cu-catalyzed approach for efficient, site-, and enantioselective coupling of readily accessible (pinacolato)alkenylboron compounds to allylic phosphates and applications to natural product synthesis.

Authors:  Fang Gao; James L Carr; Amir H Hoveyda
Journal:  J Am Chem Soc       Date:  2014-01-28       Impact factor: 15.419

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