Enantioselective and Enantiospecific Transition-Metal-Catalyzed Cross-Coupling Reactions of Organometallic Reagents To Construct C–C Bonds

Cherney, Alan H.; Kadunce, Nathaniel T.; Reisman, Sarah E.

doi:10.1021/acs.chemrev.5b00162

Cited by 796 publications

(351 citation statements)

References 479 publications

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“…[7] Up to now,o nly one nickelcatalyzed example of such ar eaction is known. [8] We hypothesized that rapid equilibration between the two enantiomers of aracemic secondary organometallic reagent [9] could enable an appropriate chiral catalyst to react preferentially with one enantiomer by ad ynamic kinetic resolution (DKR;S cheme 1c).…”

mentioning

confidence: 99%

Enantioconvergent Fukuyama Cross‐Coupling of Racemic Benzylic Organozinc Reagents

2016

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The first enantioconvergent palladium-catalyzed Fukuyama cross-coupling of racemic benzylic organozinc reagents with thioesters has been developed. The reaction furnishes enantioenriched acyclic α-disubstituted ketone products in good yields and high enantioselectivities. A broad substrate scope is achieved under mild reaction conditions to prevent racemization of the potentially labile tertiary stereocenters.

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confidence: 99%

Enantioconvergent Fukuyama Cross‐Coupling of Racemic Benzylic Organozinc Reagents

2016

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“…Would the resulting cyclobutylcopper species be produced with retention 18 or inversion 19 of configuration and would it also present some configurational stability? Thus, to the intermediate VIII , prepared as previously described from 1a with ZrCp 2 Cl 2 (20 mol%) and ethylmagnesium bromide, the corresponding cyclobutylcopper species was obtained by addition of CuI and LiCl (10 and 20 mol% respectively) at 0 °C for 15 min.…”

Section: Resultsmentioning

confidence: 99%

Zirconocene catalyzed diastereoselective carbometalation of cyclobutenes

et al. 2017

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“…Cross-coupling reactions of inert phenol derivatives by other transition metal catalysts, such as Ru [6][7][8][9][10], Fe [11,12], Co [13], Rh [14,15] and Cr [16], are beyond the scope of this review. Catalytic transformations via alkenyl [17][18][19][20][21][22][23][24][25][26][27][28] and benzylic C-O bond [29,30] activation are not covered. In addition, readers are encouraged to consult previous reviews on catalytic C-O bond activation reactions [31][32][33][34][35][36][37][38].…”

Section: Introductionmentioning

confidence: 99%

Nickel-Catalyzed Cross-Coupling Reactions of Unreactive Phenolic Electrophiles via C–O Bond Activation

2016

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Nickel-catalyzed cross-coupling reactions of aryl esters, carbamates, carbonates, ethers and arenols are reviewed. Carbon-oxygen bonds in these phenol derivatives cannot be activated by palladium, a typical cross-coupling catalyst, but a low valent nickel species in conjunction with a strong σ-donor ligand is uniquely effective for achieving this. The review is organized primarily by substrate class and secondarily by coupling partners, encompassing organometallics, heteroatom nucleophiles, C-H bonds and many others. Although the reactions in this category are covered thoroughly, each reaction is described only briefly, so that it is possible to quickly overview the spectrum of nickel-catalyzed cross-coupling reactions of inert phenol derivatives. The robustness of inert phenol derivatives under typically used catalytic conditions as well as their utility as a directing group allow unique synthetic applications of these new C-O cross-coupling reactions, which is also included in cases where appropriate. Mechanistic aspects of C-O bond activation by nickel are also summarized, highlighting their diversity compared with the C-X bond activation involved in conventional cross-coupling processes.

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Enantioselective and Enantiospecific Transition-Metal-Catalyzed Cross-Coupling Reactions of Organometallic Reagents To Construct C–C Bonds

Cited by 796 publications

References 479 publications

Enantioconvergent Fukuyama Cross‐Coupling of Racemic Benzylic Organozinc Reagents

Enantioconvergent Fukuyama Cross‐Coupling of Racemic Benzylic Organozinc Reagents

Zirconocene catalyzed diastereoselective carbometalation of cyclobutenes

Nickel-Catalyzed Cross-Coupling Reactions of Unreactive Phenolic Electrophiles via C–O Bond Activation

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