Metallaphotoredox: The Merger of Photoredox and Transition Metal Catalysis

• p. 112 Scheme 34, copper cycle, intermediate 202

  XLnCuI

• p. 31 Section 3.5 text

  affords Cu(III) intermediate 202

Only the authors can say what is right here.

Judge's note: On the page 112 image, the superscript on 202 looks like a single 'I', the same as on Cu(I) species 204. At the same resolution, the 'II' on 201 is clearly two strokes. The text on p. 31 (crop) calls 202 a Cu(III) species, and a Cu(II) complex capturing a radical would give Cu(III). Because the superscript is small in the rendered image, I am raising this as a label query for the authors, not a definite error.

Second check: another model agreed

• p. 3 Section 1.1, third paragraph

  Copper-catalyzed C−N couplings reported by Chan, Evans, and Lam

• p. 55 Reference 18

  Synthesis of Diaryl Ethers through the Copper-Promoted Arylation of Phenols with Arylboronic Acids

Judge's note: Page 3 sentence and the page 55 reference list checked. Ref 16 covers N- and O-arylations, ref 17 covers C−N, and ref 18 covers C−O diaryl ether formation, described as 'copper-promoted'. 'Chan–Evans–Lam' is a common name for the whole reaction class, so this is a wording point: the sentence attributes C−N linkages to all three reports.

Second check: another model agreed

• p. 22 Section 3.2

  The resultant benzoyl radical is proposed

• p. 100 Scheme 22 mechanism

  BzO

Judge's note: Page 100 Scheme 22: SET to (BzO)2 gives BzO• + BzO−, and BzO• converts 128 to 130, forming BzOH. 'Benzoyl radical' (PhC(O)•) names a different species; 'benzoyloxyl radical' is intended.

Second check: another model agreed

• p. 30 Section 3.5

  to the decarboxylative C−N coupling with imines,266

Only the authors can say what is right here.

Judge's note: Lines 1496–1518 of the text and the p 30 image show this. Ref 266 (Angew 2018, benzophenone imines) is first presented as the work that expanded the method to imines. The anilines paper (ref 267) is then described as a later extension. Finally ref 266 is cited again as 'subsequent work' extending the 'original protocol' to imines. The paper presents the same reference as both the base work and the later extension, so the chronology is self-contradictory. Ref 268 (Org Lett 2020) covers anilines and imines with an organic photocatalyst. Only the authors can say which citation or order was intended.

Second check: another model agreed

• p. 1 Author list, Noah B. Bissonnette

  Princeton, New Jersey 08544, United State

Judge's note: Page 1 image shows the truncated 'United State' for Bissonnette only; every other author's line reads 'United States'.

Second check: none (judge only)

• p. 5 2.1.1

  in an C(sp2)−C(sp3) decarboxylative cross-coupling

Judge's note: Page 5 image shows 'in an C(sp2)−C(sp3)'. The article is wrong whether 'C' is read as the letter or as 'carbon'.

Second check: none (judge only)

• p. 5 2.1.1

  expanding the scope CO2-

Judge's note: Page 5 image confirms that the word is missing.

Second check: none (judge only)

• p. 6 2.1.2

  the C-(sp2)−C(sp3) cross-coupling

• p. 13 2.1.5

  C-(sp3)−C(sp3) cross-electrophile coupling

Judge's note: The page 6 and page 13 images both show the hyphen after 'C' in the middle of a line, so it is not a line-break artefact.

Second check: none (judge only)

• p. 7 Section 2.1.3, end

  a photcatalytic dehydroxymethylative arylation

• p. 7 2.1.3

  a photcatalytic dehydroxymethylative arylation protocol

• p. 49 Section 7.3

  Basléand co-workers

• p. 12 Section 2.1.5

  as a key reactive intermediate,.132

Judge's note: Page 7 image shows 'photcatalytic'. Page 49 image shows 'Basléand' with no space. The 'intermediate,.' item raised in reviewer note 3 is judged under C008.

Second check: none (judge only)

• p. 12 Section 2.1.4

  the Marukami group has applied this HAT platform

• p. 37 4.3 Allylation

  Murakami likewise advanced a method for C−H allylation

• p. 60 Reference 121

  Ishida N; Masuda Y; Imamura Y; Yamazaki K; Murakami M.

• p. 40 Section 5.2

  Alcaide and Almandros.

Judge's note: Page 12 image shows 'Marukami', while ref 121 (p 60) and p 37 spell it 'Murakami'. The page 40 image shows 'Almandros' (in the first paragraph and in 'Alcaide/Almandros') and 'Almendros' later in the same section. The 'Konig' variant was not checked against an image.

Second check: none (judge only)

• p. 12 Section 2.1.5

  as a key reactive intermediate,.132

Judge's note: Page 12 image shows ',.' before superscript 132.

Second check: none (judge only)

• p. 46 6.3

  Konig and co-workers went on

• p. 14 2.1.5

  demonstrated by König and

Judge's note: I compared the p 46 and p 14 images. Ref 153 also has 'Konig'. Writing the name without the umlaut is not strictly wrong, but the paper is inconsistent.

Second check: none (judge only)

• p. 17 Section 2.2.2, end

  the expedient synthesis N-(hetero)aryl sulfamides

• p. 36 Section 4.3

  less stabilized radicals tend lead to products

• p. 41 Section 5.2, top

  ones, as well a benzofurans

• p. 48 Section 7.2

  catalytic employment Cr

Judge's note: All four phrases were seen on the page images.

Second check: none (judge only)

• p. 25 Section 3.3

  benzyloxy-azidation, and diaziation

• p. 25 3.3

  SET to azidobenzodoxole

• p. 25

  benzyloxy-azidation, and diaziation products from styrene starting materials

Judge's note: Page 25 image shows both misspellings. The ref 244 title in the text layer reads 'Azidobenziodoxole'.

Second check: none (judge only)

• p. 25 3.3

  Using [Cu-(dap)2]Cl

Judge's note: Page 25 image shows the hyphen in the middle of a line. The same page has '[Cu(dap)2]2+' and '[Cu(dap)2]PF6' with no hyphen.

Second check: none (judge only)

• p. 28 Section 3.5

  ultraviolet light-induced Ullman coupling

• p. 107 Scheme 29 title

  Photoinduced Ullman Coupling

• p. 113 Scheme 35 title

  Ullman−Goldberg Coupling

• p. 28 3.5

  across all Ullman couplings

Judge's note: Images show 'Ullman' on p 28 (text), p 107 (Scheme 29 title) and 'Ullmann−Goldberg' on p 32. The text layer confirms 'Ullman' on p 31 (line 1546) and in the Scheme 30 and 35 titles, and 'Ullmann' in refs 163, 272 and 278. So the spelling is inconsistent within the paper. Ref 218 on p 65 prints 'Subtitutions' (image checked), which is also a misspelling. All of these are cosmetic.

Second check: none (judge only)

• p. 29 Section 3.5

  than Fu and Peter's previously described

• p. 29 3.5

  than Fu and Peter’s previously described UV-active copper phenolate complexes

Judge's note: The p 29 image shows "Fu and Peter’s". The next paragraph on the same page and ref 163 ('Peters JC') give the surname as Peters, so the possessive should be Peters’.

Second check: none (judge only)

• p. 37 Section 4.4

  heterocycles the need for added chemical oxidants

• p. 37 4.4

  construction of heterocycles the need for added chemical oxidants

• p. 37 Section 4.4, first paragraph

  heterocycles the need for added chemical oxidants,

• p. 37

  heterocycles the need for added chemical oxidants,290,294

Judge's note: The p 37 image shows the sentence exactly as quoted. Without 'without' (or similar), the sentence does not parse.

Second check: none (judge only)

• p. 39 Section 5.1

  The proposed mechanism bares resemblance

Judge's note: Confirmed on the p 39 image.

Second check: none (judge only)

• p. 40 Section 5.2

  Alcaide and Almandros.342

• p. 41 Section 5.2

  Alcaide and Almandros developed the arylation/

• p. 126 Scheme 48b heading

  Alcaide/Almandros proposed 1,3-hydroxide transposition

• p. 39 5.1

  Alcaide and Almendros later found

Judge's note: The p 40 image shows 'Almandros' twice (and the text layer has a third instance in the following sentence). The p 41 image shows 'Alcaide and Almandros developed'. The p 39 image and the p 40 crop (C022) show 'Almendros'. I did not check the quoted Scheme 48b heading text, but the inconsistency in the running text is established.

Second check: none (judge only)

• p. 40 5.2

  Mourieś-Mansuy

Judge's note: The p 40 image clearly shows an acute accent over the 's', which is not a valid form of the name. Refs 344 and 348 give 'Mouries-Mansuy' (ref 344 has a stray backtick). The accent belongs on the 'e' (Mouriès), or should be omitted as in the refs.

Second check: none (judge only)

• p. 41 5.2, first line

  ones, as well a benzofurans

Judge's note: Confirmed on the p 41 image.

Second check: none (judge only)

• p. 44 Section 6.1

  asymmetric a-functionalization of ketones

• p. 44 Section 6.1

  70%−85% yield, ≥6.1 d.r.

Judge's note: The p 44 image shows an upright plain 'a', whereas elsewhere the paper uses an italic α (e.g. p 39 'α-functionalized'). The same image shows '≥6.1 d.r.' with a period. In Scheme 54 (p 132), 345–348 have 6:1, 11:1, 8:1 and 9:1 d.r., so 6:1 was intended. Both are typographic slips.

Second check: none (judge only)

• p. 45 Section 6.1

  Strongly oxidizing quinolonium photocatalyst

• p. 134 Scheme 56

  E*red = 2.46 V

Judge's note: The p 45 image shows 'quinolonium'. Scheme 56 (p 134) shows N-methylquinolinium and 3-cyano-N-methylquinolinium cations with no carbonyl, so 'quinolinium' is the intended word.

Second check: none (judge only)

• p. 49 Section 7.3

  Basléand co-workers

• p. 49 7.3

  Basléand co-workers detailed

Judge's note: The p 49 image shows 'Basléand' run together.

Second check: none (judge only)

• p. 51 Section 8, third paragraph

  between radical precursors and electrophiles in late metallaphotocatalysis, it is certainly

Only the authors can say what is right here.

Judge's note: Checked on the crop of p51. The phrase "late metallaphotocatalysis" is printed as quoted. As written it is odd: 'these metals' would have to refer back to 'Many metals' two sentences earlier. Most likely a word such as 'late-metal' or 'late transition metal' dropped out. The meaning can still be recovered, so this is minor; only the authors can confirm the intended wording.

Second check: none (judge only)

• p. 53 Biography of Edna Mao

  she joined the Macmillan research group

Judge's note: Checked on the crop of p53. The biographies just above and below on the same page spell it 'MacMillan'; Mao's has 'Macmillan'.

Second check: none (judge only)

• p. 55 Reference 13

  Matsunaga PT; Hillhouse GL; Rheingold AL Oxygen-Atom Transfer from Nitrous Oxide

• p. 62 Reference 158

  Matsunaga PT; Hillhouse GL; Rheingold AL Oxygen-Atom Transfer from Nitrous

Judge's note: Checked both entries on the images of p55 and p62. They have the same authors, title, journal, year, volume and pages. The only differences are '[cyclic]' and the 'Metallacycie' misspelling in ref 158. This is a duplicate entry, and the cited work itself is correct.

Second check: none (judge only)

• p. 65 Reference 218

  Subtitutions of Acetylenic Hydrogen with Bromalkenes

• p. 64 Reference 200

  Anilkuma G; Saranya S.

Only the authors can say what is right here.

Judge's note: Rests on outside knowledge: the published Sonogashira 1975 title ('Substitutions ... Bromoalkenes') and the editor's surname 'Anilkumar'. The page images of p65 and p64 show the text exactly as quoted. 'Subtitutions' is a plain misspelling whatever the source says.

Second check: none (judge only)

• p. 72

  Enables Alkynylative Cyclization of o-Alkylnylphenols with Iodoalkynes

Judge's note: Checked on the crop of p72. 'Alkylnyl' is printed and is not a valid chemical term; the substrates are alkynylphenols.

Second check: none (judge only)

• p. 86 Scheme 8, compound (±)-34

  Bac

Judge's note: Checked on the full image of p86. The N-protecting group on 34 reads 'Bac', while 32, 33 and the cycle intermediates read 'Boc'.

Second check: none (judge only)

• p. 96 Scheme 18, conditions

  Ir[dF(CF3)2ppy]2(bpy)PF6

Judge's note: Checked on the full image of p96. The extra '2' is printed after (CF3). Scheme 8, for example, uses Ir[dF(CF3)ppy]2(dtbbpy)PF6. The same scheme also splits 'BPin' into 'BPi n' on one intermediate.

Second check: none (judge only)

• p. 105 Scheme 27b heading

  Scope of intermolecular quinonline formation

Judge's note: Checked on the full image of p105. The heading of panel (b) prints 'quinonline'.

Second check: none (judge only)

• p. 109 Scheme 31 bullet text

  outer-shere bond formation

Judge's note: I read the banner on the page 109 image. It clearly says "outer-shere". The word is part of the scheme graphic, not the text layer, so this is not an extraction artefact.

Second check: none (judge only)

• p. 125 Scheme 47a heading

  Alknylation of arenes with terminal acetylenes

Judge's note: The page 125 image shows "Alknylation" in the panel (a) heading. The scheme caption spells it correctly ("Alkynylations").

Second check: none (judge only)

• p. 129 Scheme 51c label

  Exchange Cyle

• p. 129 Scheme 51 panel (c), blue cycle label

  Ligand Exchange Cyle

Judge's note: The page 129 image shows "Ligand Exchange Cyle" in panel (c). Both reviewer quotes refer to this same label.

Second check: none (judge only)