Proton-Coupled Electron Transfer in Organic Synthesis: Fundamentals, Applications, and Opportunities

Topics in Current Chemistry

Volumn 374, Issue 3, 2016, Pages

  Miller, David C ^a   Tarantino, Kyle T ^a   Knowles, Robert R ^a  

^a PRINCETON UNIVERSITY   (United States)

Author keywords

Free radicals; Hydrogen atom transfer; Organic synthesis; Proton coupled electron transfer

Indexed keywords

COORDINATION COMPOUND; HYDROGEN; INDOLE DERIVATIVE; ORGANIC COMPOUND; PHENOL DERIVATIVE; PROTON; QUINONE DERIVATIVE;

CHEMISTRY; ELECTRON; ELECTRON TRANSPORT; OXIDATION REDUCTION REACTION; SYNTHESIS;

COORDINATION COMPLEXES; ELECTRON TRANSPORT; ELECTRONS; HYDROGEN; INDOLES; ORGANIC CHEMICALS; OXIDATION-REDUCTION; PHENOLS; PROTONS; QUINONES;

EID: 84975818439     PISSN: 03401022     EISSN: None     Source Type: Book Series    
DOI: 10.1007/s41061-016-0030-6     Document Type: Review

References (259)

1. Migliore A, Polizzi NF, Therien MJ, Beratan DN (2014) Chem Rev 114:3381–3465
2. Reece SY, Hodgkis JM, Stubbe J, Nocera DG (2006) Philos Trans R Soc B 361:1351–1364
3. Cukier RI, Nocera DG (1998) Annu Rev Phys Chem 49:337–369
4. Mayer JM (2004) Annu Rev Phys Chem 55:363–390
5. Huynh MHV, Meyer TJ (2007) Chem Rev 107:5004–5064
6. Weinberg DR, Gagliardi CJ, Hull JF, Murphy CF, Kent CA, Westlake BC, Paul A, Ess DH, McCafferty DG, Meyer TJ (2012) Chem Rev 112:4016–4093
7. Wenger OS (2013) Acc Chem Res 46:1517–1526
8. Warren JJ, Mayer JM (2015) Biochemistry 54:1863–1878
9. Saveant J-M (2014) Annu Rev Anal Chem 7:537–560
10. Meyer TJ, Huynh MHV, Thorp HH (2007) Angew Chem Int Ed 46:5284–5304
11. Stubbe J, Nocera DG, Yee CS, Chang MCY (2003) Chem Rev 103:2167–2201
12. Minnihan EC, Nocera DG, Stubbe J (2013) Acc Chem Res 46:2524–2535
13. Kaila VRI, Verkhovsky MI, Wikström M (2010) Chem Rev 110:7062–7081
14. Lehnert N, Solomon EI (2003) J Biol Inorg Chem 8:294–305
15. Hatcher E, Soudackov A, Hammes-Schiffer S (2004) J Am Chem Soc 126:5763–5775
16. Wang Y, Chen H, Makino M, Shiro Y, Nagano S, Asamizu S, Onaka H, Shaik S (2009) J Am Chem Soc 131:6748–6762
17. Sancar A (2003) Chem Rev 103:2203–2237
18. Costentin C, Drouet S, Robert M, Saveant JM (2012) Science 338:90–94
19. Symes MD, Surendranath Y, Lutterman DA, Nocera DG (2011) J Am Chem Soc 133:5174–5177
20. Hammes-Shiffer S, Iordanova N (2004) Biochim Biophys Acta 1655:29–36
21. Hammes-Shiffer S (2012) Energy Environ Sci 5:7696
22. Green MT, Dawson JH, Gray HB (2004) Science 304:1653–1656
23. Li C, Danovich D, Shaik S (2012) Chem Sci 3:1903–1918
24. Lo JC, Yabe Y, Baran PS (2014) J Am Chem Soc 136:1304–1307
25. Iwasaki K, Wan KK, Oppedisano A, Crossley SWM, Shenvi RA (2014) J Am Chem Soc 136:1300–1303
26. King SM, Ma X, Herzon SB (2014) J Am Chem Soc 136:6884–6887
27. Choi J, Pulling ME, Smith DM, Norton JR (2008) J Am Chem Soc 130:4250–4252
28. Bordwell FG, Cheng JP, Harrelson JA (1988) J Am Chem Soc 110:1229–1231
29. Warren JJ, Tronic TA, Mayer JM (2010) Chem Rev 110:6961–7001
30. Waidmann CR, Miller AJM (2012) Ng C-WA, Scheuermann ML, Porter TR, Tronic TA, Mayer JM. Energy Environ Sci 5:7771–7780
31. Choi GC, Knowles RR (2015) J Am Chem Soc 137:9226–9229
32. Tarantino KT, Liu P, Knowles RR (2013) J Am Chem Soc 135:1002–10025
33. Salamone M, Bietti M (2015) Acc Chem Res 48:2895–2903
34. Mayer JM (2011) Acc Chem Res 44:36–46
35. Mayer JM (2011) J Phys Chem Lett 2:1481–1489
36. Both HAT and PCET have been observed to obey Marcus-type kinetics. The rate constant predicted by the Marcus cross relation is dependent on the driving force of the reaction: more favorable reactions typically result in more rapid kinetics. Consult [34] and [35] for details
37. Yayla HY, Knowles RR (2014) Synlett 20:2819–2826
38. Meyer TJ, Huynh MHV (2003) Inorg Chem 42:8140–8160
39. Binstead RA, McGuire ME, Dovletoglou A, Seok WK, Roecker LE, Meyer TJ (1992) J Am Chem Soc 114:173–186
40. Meunier B, de Visser SP, Shaik S (2004) Chem Rev 104:3947–3980
41. Hammes-Shiffer S, Soudackov AV (2008) J Phys Chem B 112:14108–14123
42. Lingwood M, Hammond JR, Hrovat DA, Mayer JM, Borden WT (2006) J Chem Theory Comput 2:740–745
43. Pesterfield LL, Maddox JB, Crocker MS, Schweitzer GK (2012) J Chem Educ 89:891–899
44. Pourbaix M (1945) Thermodynamique des solutions aqueuses diluées: représentation graphique du rôle du pH et du potentiel. Delft University of Technology, Dissertation
45. Pourbaix M (1974) Atlas of Electrochemical Equilibria in Aqueous Solution. Houston, Texas
46. Behan RK, Hoffart LM, Stone KL, Krebs C, Green MT (2006) J Am Chem Soc 128:11471–11474
47. Hayashi Y, Yamazaki I (1979) J Biol Chem 254:9101–9106
48. Green MT (2009) Curr Opin Chem Biol 13:84–88
49. Yosca TH, Behan RK, Krest CM, Onderko EL, Langston MC, Green MT (2014) J Am Chem Soc 136:9124–9131
50. Namuswe F, Kasper GD (2010) Narducci Sarjeant AA, Hayashi T, Krest CM, Green MT, Moënne-Loccoz P, Goldberg DP. J Am Chem Soc 132:157–167
51. Moyer BA, Meyer TJ (1978) J Am Chem Soc 100:3601–3603
52. Moyer BA, Meyer TJ (1981) Inorg Chem 20:436–444
53. Lebeau EL, Binstead RA, Meyer TJ (2001) J Am Chem Soc 123:10535–10544
54. Binstead RA, Moyer BA, Samuels GJ, Meyer TJ (1981) J Am Chem Soc 103:2897–2899
55. Moyer BA, Sipe BK, Meyer TJ (1981) Inorg Chem 20:1475–1480
56. Roecker L, Dobson JC, Vining WJ, Meyer TJ (1987) Inorg Chem 26:779–781
57. Gilbert JA, Gersten SW, Meyer TJ (1982) J Am Chem Soc 104:6872–6873
58. Gilbert J, Roecker L, Meyer TJ (1987) Inorg Chem 26:1126–1132
59. Seok WK, Meyer TJ (2004) Inorg Chem 43:5205–5215113
60. Gupta R, Taguchi T, Lassalle-Kaiser B, Bominaar EL, Yano J, Hendrich MP, Borovik AS (2015) Proc Nat Acad Sci. USA 112:5319–5324
61. Yano J, Kern J, Sauer K, Latimer MJ, Pushkar Y, Biesiadka J, Loll B, Saenger W, Messinger J, Zouni A, Yachandra VK (2006) Science 314:821–825
62. Britt RD, Campbell KA, Peloquin JM, Gilchrist ML, Aznar CP, Dicus MM, Robblee J, Messinger J (2004) Biochim Biophys Acta 1655:158–171
63. Yachandra VK, Sauer K, Klein MP (1996) Chem Rev 96:2927–2950
64. Gupta R, MacBeth CE, Young VG Jr, Borovik AS (2002) J Am Chem Soc 124:1136–1137
65. Gupta R, Borovik AS (2003) J Am Chem Soc 125:13234–13242
66. Borovik AS (2011) Chem Soc Rev 40:1870–1874
67. Parsell TH, Yang MY, Borovik AS (2009) J Am Chem Soc 131:2762–2763
68. Goldsmith CR, Cole AP, Stack TDP (2005) J Am Chem Soc 127:9904–9912
69. Goldsmith CR, Stack TDP (2006) Inorg Chem 45:6048–6055
70. Olmstead WN, Margolin Z, Bordwell FG (1980) J Org Chem 45:3295–3299
71. Bordwell FG, Cheng J, Ji GZ, Satish AV, Zhang X (1991) J Am Chem Soc 113:9790–9795
72. Taguchi T, Stone KL, Gupta R, Kaiser-Lassalle B, Yano J, Hendrich MP, Borovik AS (2014) Chem Sci 5:3064–3071
73. Shook RL, Peterson SM, Greaves J, Moore C, Rheingold AL, Borovik AS (2011) J Am Chem Soc 133:5810–5817
74. Baldwin MJ, Pecoraro VL (1996) J Am Chem Soc 118:11325–11326
75. Pecoraro VL, Baldwin MJ, Gelasco A (1994) Chem Rev 94:807–826
76. Amin M, Vogt L, Vassiliev S, Rivalta I, Sultan MM, Bruce D, Brudvig GW, Batista VS, Gunner MR (2013) J Phys Chem B 117:6217–6226
77. Caudle MT, Pecoraro VL (1997) J Am Chem Soc 119:3415–3416
78. Lockwood MA, Wang K, Mayer JM (1999) J Am Chem Soc 121:11894–11895
79. Larsen AS, Wang K, Lockwood MA, Rice GL, Won TJ, Lovell S, Sadilek M, Tureček F, Mayer JM (2002) J Am Chem Soc 124:10112–10123
80. Wang K, Mayer JM (1997) J Am Chem Soc 119:1470–1471
81. Thorp HH, Sarneski JE, Brudvig GW, Crabtree RH (1989) J Am Chem Soc 111:9249–9250
82. Ruettinger WF, Ho DM, Dismukes GC (1999) Inorg Chem 38:1036–1037
83. Maneiro M, Ruettinger WF, Bourles E, McLendon GL, Dismukes GC (2003) Proc Nat Acad Sci USA 100:3707–3712
84. Carrel TG, Bourles E, Lin M, Dismukes GC (2003) Inorg Chem 42:2849–2858
85. Bordwell FG, Zhang XM, Cheng JP (1993) J Org Chem 58:6410–6416
86. Kaizer J, Klinker EJ, Oh NY, Rohde JU, Song WJ, Stubna A, Kim J, Münch E, Nam W, Que L (2004) J Am Chem Soc 126:472–473
87. Price JC, Barr EW, Tirupati B, Krebs C, Bollinger JM (2003) J Am Chem Soc 125:13008–13009
88. Nesheim JC, Lipscomb JD (1996) Biochemistry 35:10240–10247
89. Kumar D, Hirao H, Que L, Shaik S (2005) J Am Chem Soc 127:8026–8027
90. Mayer JM (1998) Acc Chem Res 31:441
91. Park J, Lee YM, Nam W, Fukuzumi S (2013) J Am Chem Soc 135:5052–5061
92. Park J, Morimoto Y, Lee YM, Nam W, Fukuzumi S (2012) J Am Chem Soc 134:3903–3911
93. Wang D, Farquhar ER, Stubna A, Münch E, Que L (2009) Nature Chem 1:145–150
94. Collins MJ, Ray K, Que L (2006) Inorg Chem 45:8009–8011
95. Wang D, Que L (2013) Chem Commun 49:10682–10684
96. Sawyer DT, Sobkowiak A, Robers JL (1995) Electrochemistry for Chemists. John Wiley and Sons, New York
97. Ramdhaine B, Stern CL, Goldberg DP (2001) J Am Chem Soc 123:9447–9448
98. Goldberg DP (2007) Acc Chem Res 40:626–634
99. Baglia RA, Prokop-Prigge KA, Neu HM, Siegler MA, Goldberg DP (2015) J Am Chem Soc 137:10874–10877
100. Lansky DE, Goldberg DP (2006) Inorg Chem 45:5119–5125
101. Lansky DE, Mandimustra B, Ramdhanie B, Clausén M, Penner-Hahn J, Zvyagin SA, Telser J, Krzystek J, Zhan R, Ou Z, Kadish KM, Zakharov L, Rheingold AL, Goldberg DP (2005) Inorg Chem 44:4485–4498
102. Fukuzumi S, Kotani H, Prokop KA, Goldberg DP (2011) J Am Chem Soc 133:1859–1869
103. Prokop KA, de Visser SP, Goldberg DP (2010) Angew Chem Int Ed 49:5091–5095
104. Neu HM, Jung J, Baglia RA, Siegler MA, Ohkubo K, Fukuzumi S, Goldberg DP (2015) J Am Chem Soc 137:4614–4617
105. Boaz NC, Bell SR, Groves JT (2015) J Am Chem Soc 137:2875–2885
106. Bordwell FG (1988) Acc Chem Res 21:456–463
107. Westlake BC, Brennaman MK, Concepcion JJ, Paul JJ, Bettis SE, Hampton SD, Miller SA, Lebedeva NV, Forbes MDE, Moran M, Meyer TJ, Papanikolas JM (2011) Proc Nat Acad Sci. USA 108:8554–8558
108. Chen X, Ma G, Sun W, Dai H, Xiao D, Zhang Y, Qin X, Liu Y, Bu Y (2014) J Am Chem Soc 136:4515–4524
109. Liu W, Huang X, Cheng MJ, Nielsen RJ, Goddard WA III, Groves JT (2012) Science 337:1322–1325
110. Huang X, Bergsten TM, Groves JT (2015) J Am Chem Soc 137:5300–5303
111. Liu W, Groves JT (2010) J Am Chem Soc 132:12847–12849
112. Umile TP, Groves JT (2011) Angew Chem Int Ed 50:695–698
113. Umile TP, Wang D, Groves JT (2011) Inorg Chem 50:10353–10362
114. Svistunenko DA, Cooper CE (2004) Biophys J 87:582–595
115. Sahlin M, Graslund A, Ehrenberg A, Sjöberg BM (1982) J Biol Chem 257:366–369
116. Debus RJ, Barry BA, Babcock GT, McIntosh L (1988) Proc Nat Acad Sci. USA 85:427–430
117. Hsi LC, Hoganson CW, Babcock GT, Smith WL (199) Biochem Biophys Res Commun 202:1592–1598
118. Biczók L, Linschitz H (1995) J Phys Chem 99:1843–1844
119. Biczók L, Gupta N, Linschitz H (1997) J Am Chem Soc 119:12601–12609
120. Gupta N, Linschitz H, Biczók L (1997) Fullerene Sci Tech 5:343–353
121. Maki T, Araki Y, Ishida Y, Onomura O, Matsumura Y (2001) J Am Chem Soc 123:3371–3372
122. Costentin C, Robert M, Savéant JM (2007) J Am Chem Soc 129:9953–9963
123. Lucarini M, Mugnaini V, Pedulli GF, Guerra M (2003) J Am Chem Soc 125:8318–8329
124. Markle TF, Rhile IJ, DiPasquale AG, Mayer JM (2008) Proc Nat Acad Sci. USA 105:8185–8190
125. Markle TF, Tronic TA, DiPasquale AG, Kaminsky W, Mayer JM (2012) J Phys Chem A 116:12249–12259
126. Markle TF, Mayer JM (2008) Angew Chem Int Ed 47:738–740
127. Rhile IJ, Markle TF, Nagao H, DiPasquale AG, Lam OP, Lockwood MA, Rotter K, Mayer JM (2006) J Am Chem Soc 128:6075–6076
128. Costentin C, Robert M, Savéant JM (2010) Angew Chem Int Ed 49:3803–3806
129. Thomas F, Jarjayes O, Jamet H, Hamman S, Saint-Aman E, Duboc C, Pierre JL (2004) Angew Chem Int Ed 43:594–597
130. Reece SY, Nocera DG (2009) Annu Rev Biochem 78:673–699
131. Nagle JF, Morowitz HJ (1978) Proc Nat Acad Sci USA 75:298–302
132. Shinobu A, Agmon N (2009) J Phys Chem A 113:7253–7266
133. Chen K, Hirst J, Camba R, Bonagura CA, Stout CD, Burgess BK, Armstrong FA (2000) Nature 405:814–817
134. Rottenberg H (1998) Biochim Biophys Acta 1364:1–16
135. Wraight CA (2006) Biochim Biophys Acta 1757:886–912
136. Siegbahn PEM, Eriksson L, Himo F, Pavlov M (1998) J Phys Chem B 102:10622–10629
137. Cui Q, Karplus M (2003) J Phys Chem B 107:1071–1078
138. Sjödin M, Irebo T, Utas J, Lind J, Merényi G, Åkermark B, Hammarström L (2006) J Am Chem Soc 128:13076–13083
139. Rhile IJ, Mayer JM (2004) J Am Chem Soc 126:12718–12719
140. Sjödin M, Styring S, Åkermark B, Sun L, Hammarström L (2000) J Am Chem Soc 122:3932–3936
141. Chen J, Kuss-Peterman M, Wenger OS (2014) Chem Eur J 20:4098–4104
142. Rogge CE, Liu W, Wu G, Wang L-H, Kulmacz RJ, Tsai AL (2004) Biochemistry 43:1560–1568
143. Dempsey JL, Winkler JR, Gray HB (2010) Chem Rev 110:7024–7039
144. Gagliardi CJ, Westlake BC, Kent CA, Paul JJ, Papanikolas JM, Meyer TJ (2010) Coord Chem Rev 254:2459–2471
145. Roffey RA, Kramer DM (1994) Govindjee, Sayre RT. Biochim Biophys Acta 1185:257–270
146. Mamedov F, Sayre RT, Styring S (1998) Biochemistry 37:14245–14256
147. Svensson B, Etchebest C, Tuffery P, van Kan P, Smith J, Styring S (1996) Biochemistry 35:14486–14502
148. Wenger OS (2015) Coord Chem Rev 282–283:150–158
149. Prier CK, Rankic DA, MacMillan DWC (2013) Chem Rev 113:5322–5363
150. Concepcion JJ, Brennaman MK, Deyton JR, Lebedeva NV, Forbes MDE, Papnikolas JM, Meyer TJ (2007) J Am Chem Soc 129:6968–6969
151. Bronner C, Wenger OS (2012) J Phys Chem Lett 3:70
152. Pizano AA, Yang JL, Nocera DG (2012) Chem Sci 3:2457–2461
153. Costentin C, Louault C, Robert M, Savéant JM (2009) Proc Nat Acad Sci USA 106:18143–18148
154. Berry BW, Martinez-Rivera MC, Tommos C (2012) Proc Nat Acad Sci USA 109:9739–9743
155. Tommos C, Skalicky JJ, Pilloud DL, Wand J, Dutton DP (1999) Biochemistry 38:9495–9507
156. Martinez-Rivera MC, Berry BW, Valentine KG, Westerlund K, Hay S, Tommos C (2011) J Am Chem Soc 133:17786–17795
157. O’Dea JJ, Osteryoung J, Osteryoung RA (1981) Anal Chem 53:695–701
158. Miles AB, Compton RG (2000) J Phys Chem B 104:5331–5342
159. Glover SD, Jorge C, Liang L, Valentine KG, Hammarström L, Tommos C (2014) J Am Chem Soc 136:14039–14051
160. Zhang MT, Hammarström L (2011) J Am Chem Soc 133:8806–8809
161. Zhang MT, Nilsson J, Hammarström L (2012) Energy Environ Sci 5:7732–7736
162. Gagliardi CJ, Binstead RA, Thorp HH, Meyer TJ (2011) J Am Chem Soc 133:19594–19597
163. Wang Y, Hirao H, Chen H, Onaka H, Nagano S, Shaik S (2008) J Am Chem Soc 130:7170–7171
164. Makino M, Sugimoto H, Shiro Y, Asamizu S, Onaka H, Nagano S (2007) Proc Nat Acad Sci. USA 104:11591–11596
165. De Montellano O (ed) (2015) Cytochrome P450: Structure, Mechanism, and Biochemistry. Springer, Cham
166. Ekberg M, Pötsch S, Sandin E, Thunnissen M, Nordlund P, Sahlin M, Sjöberg BM (1998) J Biol Chem 273:21003–21008
167. Young ER, Rosenthal J, Hodgkiss JM, Nocera DG (2009) J Am Chem Soc 131:7678–7684
168. Hodgkiss JM, Damrauer NH, Pressé S, Rosenthal J, Nocera DG (2006) J Phys Chem B 110:18853–18858
169. Pressé S, Silbey R (2006) J Chem Phys 124:164504
170. Clare LA, Pham AT, Magdaleno F, Acosta J, Woods JE, Cooksy AL, Smith DK (2013) J Am Chem Soc 135:18930
171. Alligrant TM, Alvarez JC (2011) J Phys Chem C 115:10797–10805
172. Nordlund P, Eklund H (1993) J Mol Bio 232:123–164
173. Nordlund P, Sjöberg BM, Eklund H (1990) Nature 345:593–598
174. Hogböm M, Galander M, Andersson M, Kolberg M, Hofbauer W, Lassman G, Nordlund P, Lendzian F (2003) Proc Nat Acad Sci USA 100:3209–3214
175. Himo F, Seigbahn PEM (2003) Chem Rev 103:2421–2456
176. Lendzian F (2005) Biochim Biophys Acta 1707:67–90
177. Lendzian F, Sahlin M, MacMillan F, Bittl R, Fiege R, Pötsch S, Sjöberg BM, Gräslund A, Lubitz W, Lassmann G (1996) J Am Chem Soc 118:8111–8120
178. Byrdin M, Eker APM, Vos MH, Brettel K (2003) Proc Nat Acad Sci USA 100:8676–8681
179. Aubert C, Vos MH, Mathis P, Eker APM, Brettel K (2000) Nature 405:586–590
180. Zieba AA, Richardson C, Lucero C, Dieng SD, Gindt YM, Schelvis JPM (2011) J Am Chem Soc 133:7824–7836
181. Kapetanaki SM, Ramsey M, Gindt YM, Schelvis JPM (2004) J Am Chem Soc 126:6214
182. Byrdin M, Sartor V, Eker APM, Vos MH, Aubert C, Brettel K, Mathis P (2004) Biochim Biophys Acta 1655:64–70
183. Shih C, Museth AK, Abrahamsson M, Blanco-Rodriguez AM, Di Bilio AJ, Sudhamsu J, Crane BR, Ronayne KL, Towrie M, Vlcek A Jr, Richards JH, Winkler JR, Gray HB (2008) Science 320:1760–1762
184. Stoll S, Shafaat HS, Krzystek J, Ozarowski A, Tauber MJ, Kim JE, Britt RD (2011) J Am Chem Soc 133:18098
185. Farver O, Skov LK, Young S, Bonander N, Karlsson BG, Vännguard T, Pecht I (1997) J Am Chem Soc 119:5453–5454
186. Fujita K, Nakamura N, Ohno H, Leigh BS, Niki K, Gray HB, Richards JH (2004) J Am Chem Soc 126:13954–13961
187. Gilardi G, Mei G, Rosato N, Canters GW, Finazzi-Agrò A (1994) Biochemistry 33:1425
188. Gagliardi CJ, Murphy CF, Binstead RA, Thorp HH, Meyer TJ (2015) J Phys Chem C 119:7028–7038
189. Medina-Ramos J, Oyesanya O, Alvarez JC (2013) J Phys Chem C 117:902–912
190. Kuss-Peterman M, Wenger OS (2013) J Phys Chem Lett 4:2535–2539
191. Griesbaum K (1970) Angew Chem Int Ed 9:273–287
192. Heiba EAI, Dessau RM (1967) J Org Chem 32:3837–3840
193. Hoyle CE, Bowman CN (2010) Angew Chem Int Ed 49:1540–1573
194. Tyson EL (2014) Niemeyer Zl, Yoon TP. J Org Chem 79:1427–1436
195. LeBel NA, DeBoer A (1967) J Am Chem Soc 89:2784–2785
196. Benati L, Leardini R, Minozzi M, Nanni D, Scialpi R, Spagnolo P, Strazzari S, Zanardi G (2004) Angew Chem Int Ed 43:3598–3601
197. Denes F, Pichowicz M, Povie G, Renaud P (2014) Chem Rev 114:2587–2693
198. Dang HS, Kim KM, Roberts BP (1998) Chem Commun 1413–1414
199. Zhao R, Lind J, Merenyi G, Eriksen TE (1994) J Am Chem Soc 116:12010–12015
200. Fujisawa H, Hayakawa Y, Sasaki Y, Mukaiyama T (2001) Chem Lett 30:632–633
201. Huyser ES, Kellogg RM (1966) J Org Chem 31:3366–3369
202. Dang HS, Roberts BP (1999) Tet Lett 40:8929–8933
203. Kemper J, Studer A (2005) Angew Chem Int Ed 44:4914
204. Qvortrup K, Rankic DA, MacMillan DWC (2014) J Am Chem Soc 136:626–629
205. Hager D, MacMillan DWC (2014) J Am Chem Soc 136:16986–16989
206. Li JN, Liu L, Fu Y, Guo QX (2006) Tetrahedron 62:4453–4462
207. Kolthoff IM, Chantooni MK, Bhowmik S (1968) J Am Chem Soc 90:23–28
208. Newcomb M, Esker JL (1991) Tetrahedron Lett 32:1035–1038
209. Boivin J, Callier-Dublanchet AC, Quiclet-Sire B, Schiano AM, Zard SZ (1995) Tetrahedron 51:6517–6528
210. Guin J, Frolich R, Studer A (2008) Angew Chem Int Ed 47:779–782
211. Choi CM, Guin J, Mück-Lichtenfeld C, Grimme S, Studer A (2011) Chem-Asian J 6:1197–1209
212. Nicolaou KC, Baran PS, Zhong YL, Barluenga S, Hunt KW, Kranich R, Vega JA (2002) J Am Chem Soc 124:2233–2244
213. Tang Y, Li C (2004) Org Lett 6:3229–3231
214. Li Z, Song L, Li C (2013) J Am Chem Soc 135:4640–4643
215. While many reactions presented throughout the review are done so as closed catalytic cycles, the community has become increasingly aware of potential chain mechanisms. In all instances, we defer to the mechanism presented by the author. For more information, consult: Cismesia MA, Yoon TP (2015) Chem Sci 6:5426–5434
216. Hanss D, Freys JC, Bernardinelli GR, Wenger OS (2009) Eur J Inorg Chem 2009:4850–4859
217. Warren JJ, Menzeleev AR, Kretchmer JS, Miller TF III, Gray HB, Mayer JM (2013) J Phys Chem Lett 4:519–523
218. Warren JJ, Mayer JM (2011) J Am Chem Soc 133:8544–8551
219. Schrauben JN, Cattaneo M, Day TC, Tenderholt AL, Mayer JM (2012) J Am Chem Soc 134:16635–16645
220. Megiatto JD Jr, Méndez-Hernández DD, Tejeda-Ferrari ME, Teillout AL, Llansola-Portolés MJ, Kodis G, Moore TA, Moore AL (2014) Nat Chem 6:423–428
221. Edwards SJ, Soudackov AV, Hammes-Schiffer S (2009) J Phys Chem A 113:2117–2126
222. Miller DC, Choi GC, Orbe HS, Knowles RR (2015) J Am Chem Soc 137:13492–13495
223. Estes DP, Grills DC, Norton JR (2014) J Am Chem Soc 136:17362–17365
224. Roth JP, Mayer JM (1999) Inorg Chem 38:2760–2761
225. Manner VW, Mayer JM (2009) J Am Chem Soc 131:9874–9875
226. Jonas RT, Stack TDP (1997) J Am Chem Soc 119:8566–8567
227. Semproni SP, Milsmann C, Chirik PJ (2014) J Am Chem Soc 136:9211–9224
228. Fang H, Ling Z, Lang K, Brothers PJ, Bruin B, Fu X (2014) Chem Sci 5:916–921
229. Miyazaki S, Kojima T, Mayer JM, Fukuzumi S (2009) J Am Chem Soc 131:11615–11624
230. Wu A, Mayer JM (2008) J Am Chem Soc 130:14745–14754
231. Wu A, Masland J, Swartz RD, Kaminsky W, Mayer JM (2007) Inorg Chem 46:11190–11201
232. Mislmann C, Semproni SP, Chirik PJ (2014) J Am Chem Soc 136:12099–12107
233. Tarantino KT, Miller DC, Callon TA, Knowles RR (2015) J Am Chem Soc 137:6440–6443
234. Huang K, Han JH, Cole AP, Musgrave CB, Waymouth RM (2005) J Am Chem Soc 127:3807–3816
235. Huang K, Han JH, Musgrave CB, Waymouth RM (2006) Organometallics 25:3317–3323
236. Gansauer A, von Laugenberg D, Kube C, Dahmen T, Michelmann A, Behlendorf M, Sure R, Seddiqzai M, Grimme S, Sadasivam DV, Fianu GD, Flowers RA (2015) Chem Eur J 21:280–289
237. Jeftic L, Manning G (1970) J Electroanal Chem 26:195–200
238. Quan M, Sanchez D, Wasylkiw MF, Smith DK (2007) J Am Chem Soc 129:12847–12856
239. Gupta N, Linschitz H (1997) J Am Chem Soc 119:6384–6391
240. Okamoto K, Ohkubo K, Kadish KM, Fukuzumi S (2004) J Phys Chem A 108:10405–10413
241. Gomez M, Gomez-Castro CZ, Padilla-Martinez II, Martinez-Martinez FJ, Gonzalez FJ (2004) J Electroanal Chem 567:269–276
242. Fukuzumi S, Ishikawa K, Hironaka K, Tanaka T (1987) J Chem Soc Perkin Trans II:751–760
243. Fukuzumi S, Ishikawa M, Tanaka T (1989) J Chem Soc Perkin Trans II:1811–1816
244. Ishikawa M, Fukuzumi S (1990) J Chem Soc, Faraday Trans 86:3531–3536
245. Yuasa J, Yamada S, Fukuzumi S (2008) J Am Chem Soc 130:5808–5820
246. Zhai L, Shukla R, Wadumethrige SH, Rathore R (2010) J Org Chem 75:4748–4760
247. Turek AK, Hardee DJ, Ullman AM, Nocera DG, Jacobsen EN (2015) Angew Chem Int Ed 54: doi:10.1002/ange.201508060
248. Bock CR, Connor JA, Gutierrez AR, Meyer TJ, Whitten DG, Sullivan BP, Nagle JK (1997) J Am Chem Soc 101:4815–4824
249. Fukuzumi S, Mochizuki S, Tanaka T (1989) J Am Chem Soc 111:1497–1499
250. Fukuzumi S, Mochizuki S, Tanaka T (1990) J Phys Chem 94:722–726
251. Ishikawa M, Fukuzumi S (1990) J Chem Soc Chem Commun 1353–1355
252. Fukuzumi S, Kuroda S, Goto T, Ishikawa K, Tanaka T (1989) J Chem Soc Perkin Trans II:1047–1053
253. Du J, Espelt LR, Guzei IA, Yoon TP (2011) Chem Sci 2:2115–2119
254. Ischay MA, Anzovino ME, Du J, Yoon TP (2008) J Am Chem Soc 130:12886–12887
255. Du J, Yoon TP (2009) J Am Chem Soc 131:14604–14605
256. Rono LJ, Yayla HY, Wang DY, Armstrong MF, Knowles RR (2013) J Am Chem Soc 135:17735–17738
257. Nakajima M, Fava E, Loescher S, Jiang Z, Rueping M (2015) Angew Chem Int Ed 54:8828–8832
258. Mercer GJ, Sigman MS (2003) Org Lett 5:1591–1594
259. DiRocco DA, Dykstra K, Krska S, Vachal P, Conway DV, Tudge M (2014) Angew Chem Int Ed 53:4802–4806