Pd(II)-Catalyzed C–H Activation/C–C Cross-Coupling Reactions: Versatility and Practicality

• p. 16 Reference 71

  J Am Chem Soc 2008;130ASAP

Only the authors can say what is right here.

Judge's note: The p.16 crop shows the entry as quoted. It gives a volume but only 'ASAP' in place of pages, so the citation is incomplete. This is an author manuscript and the reference was probably in press, but only the authors can supply the final pages.

Second check: another model agreed

• p. 8 Section 6.4

  in that the latter have unusually high thermodynamic

• p. 8 Section 6.4, paragraph after Scheme 46

  the latter have unusually high thermodynamic stability. The stability of such C–H insertion intermediates is beneficial

• p. 2 Introduction, CIPE paragraph

  thermodynamic stability of the resulting intermediates in the case of the CIPE is generally much lower

Only the authors can say what is right here.

Judge's note: On p8, 'the latter' assigns high stability to the cyclopalladated complexes. The next sentence attributes the double-edged stability to 'such C–H insertion intermediates', and p2 says CIPE intermediates' stability 'is generally much lower'. The second sentence most likely refers to the cyclopalladated complexes, but as written the referent is ambiguous. The authors should clarify.

Second check: another model agreed

• p. 3 Section 2

  triflate-protected arylalkylamines

• p. 9 Section 6.4

  triflate-protected phenylalkyl amines

• p. 30 Scheme 13

  NHTf

• p. 12 Section 7, Conclusions

  of simple substrates with this Pd(II)/Pd(0) coupling such as carboxylic acids and amines, has

Judge's note: Scheme 13 (p30) draws ArCH2(CH2)nNHTf, and the p3 sentence itself calls these 'triflamide groups'. 'Triflate-protected' is a loose name for an N-triflyl group. This is a minor nomenclature point. The second reviewer's point about the conclusions ('carboxylic acids and amines, has been achieved', p12) is a matter of how strongly the claim is put: p9 does report that these amines 'similarly undergo successful ortho-coupling under identical conditions' as ongoing work. I do not adopt it as a separate defect.

Second check: another model agreed

• p. 3 Section 3, first paragraph

  despite the early proposal of the existence of this oxidation state[26,27]

• p. 14 Reference 26

  For early proposal of formation of Pt(IV) complexes, see: Pope WJ, Peachy SJ.

Only the authors can say what is right here.

Judge's note: I checked the p3 sentence and the ref 26 entry on p14. Both parts of ref 26 are explicitly about platinum. The authors may intend the Pt(IV) precedent as an analogy, but as written 'this oxidation state' means Pd(IV). The authors should clarify.

Second check: another model agreed

• p. 61 Scheme 44, structures A and B; caption

  A working model for table salt-promoted C–H insertion

• p. 8 Section 6.4

  In our working model, the sodium cation coordinates with the carboxylate group

Judge's note: On p.61, A and B show K⊕ on the carboxylate; only the lower equation uses Na. The text on p.8 describes the model with Na+ but also says a wide range of counter-ions, including Na+ and K+, are effective. So drawing K+ is chemically defensible, but it does not match the caption and the text. This is a minor consistency point.

Second check: another model agreed

• p. 9 Section 6.4

  As shown for pyridyl boronic acid substrates, 2,6-disubstitution is required

• p. 90 Table 3 title

  Coupling with heterocyclic trifluoroborates

• p. 9 Section 6.4, paragraph on phenyl acetic acids

  Currently, the scope of heterocyclic boronic acids is still limited (Table 3). As shown for pyridyl boronic acid substrates

Judge's note: I checked p9 and Table 3 on p90. The table's reagent is a 2-fluoro-6-methylpyridin-3-yl BF3K salt. The paper distinguishes ArBF3K from boronic acids elsewhere (p8, Table 1), so 'boronic acids' misnames the reagent class used in Table 3.

Second check: another model agreed

• p. 2 Introduction, 2nd paragraph

  driven by not only by traditional

Judge's note: I checked the p2 crop. The doubled 'by' appears in the rendered text.

Second check: none (judge only)

• p. 3 Section 2, last paragraph

  hinderance

• p. 3 Section 2, meta-olefination paragraph

  steric hinderance

• p. 3 Section 2, meta-C–H activation paragraph

  steric hinderance seem to govern

Judge's note: I checked the p3 crop. The text reads 'steric hinderance'. All three locators point to this single occurrence in the meta-olefination paragraph.

Second check: none (judge only)

• p. 32 Scheme 15 caption

  electronic-deficient arenes

• p. 32 Scheme 15 caption

  meta-Selective olefination of electronic-deficient arenes

• p. 3 Section 2 text

  C–H activation of electron-deficient arenes

Judge's note: The p.32 crop shows 'electronic-deficient'. The text on p.3 uses 'electron-deficient arenes'.

Second check: none (judge only)

• p. 4 Section 4 heading

  Pd(0)//Pd(II)/Pd

• p. 4 Section 4 heading

  Pd(0)//Pd(II)/Pd (IV) Catalysis

Judge's note: The p4 crop shows the double slash in the rendered heading. The conclusions write 'Pd(0)/Pd(II)/Pd(IV)'.

Second check: none (judge only)

• p. 4 Section 3, 2nd paragraph

  after the completion the asymmetric

• p. 4

  the isolation of quantitative amounts of PdI2 after the completion the asymmetric

Judge's note: I checked the p4 crop. The word is missing in the rendered text.

Second check: none (judge only)

• p. 5 Section 5, Scheme 31 paragraph

  bromides (Scheme 31).7i However

• p. 5 Section 5, pivalic acid paragraph

  (Scheme 31).7i However

Judge's note: The p5 crop shows the plain '7i' in-line, while every other citation in the text is bracketed.

Second check: none (judge only)

• p. 5 Section 5, last paragraph

  this finding inspired for our own recent studies

Judge's note: I checked the p5 crop. The extra 'for' is in the rendered text.

Second check: none (judge only)

• p. 47 Scheme 30 caption

  benzadehydes

• p. 47 Scheme 30 caption

  ortho-Arylation of benzanilides, benzadehydes and benzoic acids

• p. 5 Section 5 text

  benzanilides, benzaldehydes and benzoic acids

Judge's note: The p.47 crop shows 'benzadehydes'. The text on p.5 spells it 'benzaldehydes'.

Second check: none (judge only)

• p. 8 Section 6.4, 1st paragraph

  was major hurdle to clear

Judge's note: I checked on the p8 page image.

Second check: none (judge only)

• p. 8 Section 6.4, 3rd paragraph

  the presence of wide range of cationic counter ions

Judge's note: I checked on the p8 page image.

Second check: none (judge only)

• p. 11 Section 6.7, 1st paragraph

  emerged as promising asymmetric C–H amination method

Judge's note: The crop of p.11 shows the sentence exactly as quoted. It should read 'as a promising … method'.

Second check: none (judge only)

• p. 74 Scheme 57 caption

  Desymmetrization of germinal aryl and methyl groups

• p. 11 Section 6.7 text

  prochiral C–H bonds on geminal aryl or methyl groups

Judge's note: The page-74 crop shows the caption spelled 'germinal'. The body text on p11 uses 'geminal', which is the correct chemical term. This is a plain misspelling.

Second check: none (judge only)

• p. 12 Section 7, first sentence

  a promising set of synthetic transformation

• p. 12 Conclusions

  a promising set of synthetic transformation for the assembly

Judge's note: Seen on the page 12 crop, first sentence of Conclusions and Outlook. 'set of' needs the plural.

Second check: none (judge only)

• p. 12 Section 6.7

  bisdentate coordination of the ligand

• p. 12

  a process that hinges upon the bisdentate coordination of the ligand

Judge's note: The p.12 crop shows 'bisdentate'. The standard term is 'bidentate'.

Second check: none (judge only)

• p. 13 Conclusions, last bullet

  based the results of our laboratory

• p. 13 Conclusions, enantioselective bullet

  based the results of our laboratory to date

Judge's note: The p.13 crop shows 'based the results' with no 'on' and 'Although,' with a comma.

Second check: none (judge only)

• p. 13 Acknowledgments

  the U.S. National Institute of Health

• p. 13 Acknowledgments

  National Institute of Health

Only the authors can say what is right here.

Judge's note: Rests on outside knowledge: the agency's official name is 'National Institutes of Health'. The p.13 crop shows 'National Institute of Health' as quoted.

Second check: none (judge only)

• p. 16 Reference 73

  73. Beak P, Snieckus V. Acc Chem Res 1982;15:306.

• p. 14 Reference 8a

  Beak P, Snieckus V. Acc Chem Res 1982;15:306.

• p. 14 Reference 8a

  a) Beak P, Snieckus V. Acc Chem Res 1982;15:306.

Judge's note: The p.16 crop (ref. 73) and the p.14 crop (ref. 8a) show identical bibliographic data. Listing the same work twice is a copy-editing redundancy only; no citation points to the wrong work.

Second check: none (judge only)

• p. 17 Reference 86

  Angew Chem Int Ed 2004;43:2206.

• p. 14 Reference 8d

  Angew Chem Int Ed 2004;43:2206.

• p. 17 Reference 86

  Whisler MC, MacNeil S, Snieckus V, Beak P.

• p. 14 Reference 8d

  d) Whisler MC, MacNeil S, Snieckus V, Beak P. Angew Chem Int Ed 2004;43:2206.

Judge's note: The p.17 crop (ref. 86) and the p.14 crop (ref. 8d) cite the same article. Ref. 86 also gives the German edition and adds context ('For enantioselective lithiation…'). This is a redundancy, not a wrong citation.

Second check: none (judge only)

• p. 15 Reference 38b

  Crdenas DJ, Martn-Matute B

• p. 15 Reference 38b

  Crdenas DJ, Martn-Matute B, Echavarren AM

Only the authors can say what is right here.

Judge's note: Rests on outside knowledge: the names are Cárdenas and Martín-Matute. On the p.15 page image the letters are missing from the rendered text itself ('Crdenas', 'Martn-Matute'), so this is not an extraction artefact. Ref. 7j on p.14 renders 'García' correctly, which suggests the drop is specific to this entry.

Second check: none (judge only)

• p. 17 Reference 94

  Gendre PL, Yamada

• p. 17 Reference 94

  Gendre PL, Yamada yA, Ohtaki H

Only the authors can say what is right here.

Judge's note: Rests on outside knowledge: the authors are Le Gendre P and Yamada A. The p.17 crop shows 'Gendre PL, Yamada yA' on the page. 'yA' is plainly malformed whatever the correct name is.

Second check: none (judge only)

• p. 63 Scheme 46, second header

  Giri, R.; Yu, J. 2007

• p. 58 Scheme 41 header

  Chen, X.; Yu, J. Q. 2006

Judge's note: Checked on the p.63 and p.58 page images. Scheme 46 shows 'Maugel, N.; Yu, J.-Q.' and then 'Giri, R.; Yu, J.'; Scheme 41 shows 'Yu, J. Q.'. This is cosmetic.

Second check: none (judge only)