Palladium-catalyzed sp 3 C H activation. Yan Xu Dong Group Meeting Apr. 2, 2014
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1 Palladium-catalyzed sp 3 C H activation, Yan Xu Dong Group Meeting Apr. 2, 2014
2 Content 1 Allylic C H activation 2 Benzylic C H activation Palladiumcatalyzed sp 3 C H activation 3 4 Common sp 3 C H activation: Direct C X bond formation Common sp 3 C H activation: Direct C C bond formation 5 Summary
3 Content 1 Allylic C H activation 2 Benzylic C H activation Palladiumcatalyzed sp 3 C H activation 3 4 Common C H activation: Direct C X bond formation Common C H activation: Direct C C bond formation 5 Summary
4 Allylic C H activation: direct carboxylation Easiest C-H bond to activate allylic C H oxidation using stoichiometric palladium(ii): 1960s allylic alkylation from prepared allyl Pd complexes reported by Trost: 1970s W. G. Young, J. Am. Chem. Soc., 1966, 88, 2054 P. G. C. Campbell, J. Am. Chem. Soc., 1971, 93, 1497 P. G. C. Campbell, J. Am. Chem. Soc., 1971, 93, 1499 B. M. Trost and T. J. Fullerton, J. Am. Chem. Soc., 1973, 95, 1780
5 Allylic C H activation: direct carboxylation First report by White M. C. White, J. Am. Chem. Soc., 2004, 126, Macrolactonization M. C. White, J. Am. Chem. Soc., 2006, 128, 9032.
6 Allylic C H activation: direct carboxylation First report by White M. C. White, J. Am. Chem. Soc., 2004, 126, Macrolactonization M. C. White, J. Am. Chem. Soc., 2006, 128, 9032.
7 Allylic C H activation: direct carboxylation Real ligand Stoichiometric experiment Mechanism J. Am. Chem. Soc., 2005, 127, For other RCOOH as substrates, see: J. Am. Chem. Soc., 2010, 132,
8 Allylic C H activation: direct carboxylation Real ligand Stoichiometric experiment Mechanism J. Am. Chem. Soc., 2005, 127, For other RCOOH as substrates, see: J. Am. Chem. Soc., 2010, 132,
9 Allylic C H activation: direct carboxylation allylic C H oxidation/vinylic C H arylation M. C. White, J. Am. Chem. Soc., 2006, 128, asymmetric allylic C H oxidation M. C. White, Angew. Chem., Int. Ed., 2008, 47, 6448.
10 Allylic C H activation: direct carboxylation allylic C H oxidation/vinylic C H arylation M. C. White, J. Am. Chem. Soc., 2006, 128, asymmetric allylic C H oxidation M. C. White, Angew. Chem., Int. Ed., 2008, 47, 6448.
11 Allylic C H activation: direct carboxylation allylic C H oxidation with O 2 K. Kaneda, Angew. Chem., Int. Ed., 2006, 45, 481. allylic C H acetoxylation S. S. Stahl, J. Am. Chem. Soc., 2010, 132,
12 Allylic C H activation: direct carboxylation allylic C H oxidation with O 2 K. Kaneda, Angew. Chem., Int. Ed., 2006, 45, 481. allylic C H acetoxylation S. S. Stahl, J. Am. Chem. Soc., 2010, 132,
13 Allylic C H activation: Direct amination 1,2-amino alcohol scaffold 1,3-amino alcohol scaffold M. C. White, J. Am. Chem. Soc., 2007, 129, M. C. White, J. Am. Chem. Soc., 2009, 131,
14 Allylic C H activation: Direct amination 1,2-amino alcohol scaffold 1,3-amino alcohol scaffold M. C. White, J. Am. Chem. Soc., 2007, 129, M. C. White, J. Am. Chem. Soc., 2009, 131,
15 Allylic C H activation: Direct amination G. Liu, Org. Lett., 2009, 11, 2707 Intermolecular version M. C. White, J. Am. Chem. Soc., 2008, 130, Cr(III) can be replaced by 6% DIPEA, see: M. C. White, J. Am. Chem. Soc., 2009, 131,
16 Allylic C H activation: Direct amination G. Liu, Org. Lett., 2009, 11, 2707 Intermolecular version M. C. White, J. Am. Chem. Soc., 2008, 130, Cr(III) can be replaced by 6% DIPEA, see: M. C. White, J. Am. Chem. Soc., 2009, 131,
17 Allylic C H activation: Direct amination Intermolecular C-H amination G. Liu, Angew. Chem., Int. Ed., 2008, 47, PhI(OPiv) 2 as the oxidant G. Liu, J. Am. Chem. Soc., 2010, 132,
18 Allylic C H activation: Direct amination Intermolecular C-H amination G. Liu, Angew. Chem., Int. Ed., 2008, 47, PhI(OPiv) 2 as the oxidant G. Liu, J. Am. Chem. Soc., 2010, 132,
19 Allylic C H activation: Direct amination Proposed mechanism: P. S. Baran, Angew. Chem., Int. Ed., 2009, 48, 7025.
20 Allylic C H activation: Direct C C bond formation Intermolecular C-H alkylation Shi s work Z.-J. Shi, J. Am. Chem. Soc., 2008, 130, White s work M. C. White, J. Am. Chem. Soc., 2008, 130, 14090
21 Content 1 Allylic C H activation 2 Benzylic C H activation Palladiumcatalyzed sp 3 C H activation 3 4 Common sp 3 C H activation: Direct C X bond formation Common sp 3 C H activation: Direct C C bond formation 5 Summary
22 Content 1 Allylic C H activation 2 Benzylic C H activation Palladiumcatalyzed sp 3 C H activation 3 4 Common sp 3 C H activation: Direct C X bond formation Common sp 3 C H activation: Direct C C bond formation 5 Summary
23 Benzylic C H activation: Direct acetoxylation / fluorination C-H acetoxylation C-H fluorination M. S. Sanford, J. Am. Chem. Soc., 2004, 126, 2300 Thermo 110 o C: 36% out of 82% conversion μwave 110 o C: 75% out of 97% conversion M. S. Sanford, J. Am. Chem. Soc., 2006, 128, 7134.
24 Benzylic C H activation: Direct acetoxylation / fluorination C-H acetoxylation C-H fluorination M. S. Sanford, J. Am. Chem. Soc., 2004, 126, 2300 Thermo 110 o C: 36% out of 82% conversion μwave 110 o C: 75% out of 97% conversion M. S. Sanford, J. Am. Chem. Soc., 2006, 128, 7134.
25 Benzylic C H activation: Direct acetoxylation / fluorination C-H acetoxylation C-H fluorination M. S. Sanford, J. Am. Chem. Soc., 2004, 126, % M. S. Sanford, Org. Lett. 2012, 14, 4094
26 Benzylic C H activation: Direct acetoxylation / fluorination M. S. Sanford, Angew. Chem. Int. Ed 2012, 51, 3414 M. S. Sanford, J. Am. Chem. Soc. 2014, 136, 4097
27 Benzylic C H activation: Direct acetoxylation / fluorination M. S. Sanford, Angew. Chem. Int. Ed 2012, 51, 3414 M. S. Sanford, J. Am. Chem. Soc. 2014, 136, 4097
28 Benzylic C H activation: Direct C C bond formation C-H arylation M. S. Sanford, J. Am. Chem. Soc., 2005, 127, M. S. Sanford, J. Am. Chem. Soc., 2009, 131,
29 Benzylic C H activation: Direct C C bond formation C-H arylation M. S. Sanford, J. Am. Chem. Soc., 2005, 127, M. S. Sanford, J. Am. Chem. Soc., 2009, 131, O. Daugulis, Org. Lett., 2005, 7, 3657.
30 Benzylic C H activation: Direct C C bond formation K. Fagnou, J. Am. Chem. Soc., 2008, 130, C-H alkylation Mechanism: H. Huang, J. Am. Chem. Soc., 2010, 132, 3650.
31 Benzylic C H activation: Direct C C bond formation K. Fagnou, J. Am. Chem. Soc., 2008, 130, C-H alkylation Mechanism: H. Huang, J. Am. Chem. Soc., 2010, 132, 3650.
32 Content 1 Allylic C H activation 2 Benzylic C H activation Palladiumcatalyzed sp 3 C H activation 3 4 Common sp 3 C H activation: Direct C X bond formation Common sp 3 C H activation: Direct C C bond formation 5 Summary
33 Content 1 Allylic C H activation 2 Benzylic C H activation Palladiumcatalyzed sp 3 C H activation 3 4 Common sp 3 C H activation: Direct C X bond formation Common sp 3 C H activation: Direct C C bond formation 5 Summary
34 Common C H activation: Direct C X bond formation General model Pathway A: triggered by C-H cleavage Pathway B: triggered by OA
35 Common C H activation: Direct C X bond formation General model Pathway A: triggered by C-H cleavage Pathway B: triggered by OA
36 C.-M. Che, JACS., 2006, 128, Common C H activation: Direct C X bond formation C-H actoxylation M. S. Sanford, JACS., 2004, 126, C-H amidation M. S. Sanford, Org. Lett., 2010, 12, 532
37 C.-M. Che, JACS., 2006, 128, Common C H activation: Direct C X bond formation C-H actoxylation M. S. Sanford, JACS., 2004, 126, C-H amidation M. S. Sanford, Org. Lett., 2010, 12, 532
38 C.-M. Che, JACS., 2006, 128, Common C H activation: Direct C X bond formation C-H actoxylation M. S. Sanford, JACS., 2004, 126, C-H amidation M. S. Sanford, Org. Lett., 2010, 12, 532
39 Common C H activation: Direct C X bond formation C-H iododination For a diiodination version followed by converting into cyclopropane, see: J.-Q. Yu, Org. Lett., 2006, 8, J.-Q. Yu, Angew. Chem., Int. Ed., 2005, 44, 2112 C-H acetoxylation J.-Q. Yu, Angew. Chem., Int. Ed., 2005, 44, 7420.
40 Common C H activation: Direct C X bond formation C-H iododination For a diiodination version followed by converting into cyclopropane, see: J.-Q. Yu, Org. Lett., 2006, 8, J.-Q. Yu, Angew. Chem., Int. Ed., 2005, 44, 2112 C-H acetoxylation J.-Q. Yu, Angew. Chem., Int. Ed., 2005, 44, 7420.
41 Common C H activation: Direct C X bond formation Mechanism study J.-Q. Yu, Angew. Chem., Int. Ed., 2005, 44, J.-Q. Yu, Org. Lett., 2006, 8, 3387.
42 Common C H activation: Direct C X bond formation Mechanism study J.-Q. Yu, Angew. Chem., Int. Ed., 2005, 44, J.-Q. Yu, Org. Lett., 2006, 8, 3387.
43 Common C H activation: Direct C X bond formation intramolecular direct amidation F. Glorius, Angew. Chem., Int. Ed., 2009, 48, 6892.
44 Common C H activation: Direct C C bond formation triggered by OA Mechanism: G. Dyker, Angew. Chem., Int. Ed.., 1992, 31, 1023.
45 Common C H activation: Direct C C bond formation triggered by OA Mechanism: G. Dyker, Angew. Chem., Int. Ed.., 1992, 31, G. Dyker, Angew. Chem., Int. Ed., 1994, 33, 103.
46 Common C H activation: Direct C C bond formation triggered by OA S. L. Buchwald, JACS., 2005, 127, 4685
47 Common C H activation: Direct C C bond formation triggered by OA J.-Q. Yu, J. Am. Chem. Soc., 2009, 131, 9886 For detailed discussion for cation-promoted Pd insertion into C-H bonds, see: Yu, J.-Q. J. Am. Chem. Soc. 2008, 130,
48 Common C H activation: Direct C C bond formation triggered by OA J.-Q. Yu, J. Am. Chem. Soc., 2009, 131, 9886 J.-Q. Yu, Tetrahedron, 2010, 66, 4811.
49 Common C H activation: Direct C C bond formation triggered by OA J.-Q. Yu, J. Am. Chem. Soc., 2009, 131, 9886 J.-Q. Yu, G. Musaev, J. Am. Chem. Soc. 2013, 135, 14206
50 Common C H activation: Direct C C bond formation triggered by OA J.-Q. Yu, J. Am. Chem. Soc., 2009, 131, 9886 For alkynylation, also see: M. Tobisu, N. Chatani J. Am. Chem. Soc., 2011, 133, J.-Q. Yu,, J. Am. Chem. Soc. 2013, 135, 3387
51 Common C H activation: Direct C C bond formation triggered by OA O. Baudoin, Angew. Chem., Int. Ed., 2003, 42, R = Et, 74% Mechanism:
52 Common C H activation: Direct C C bond formation triggered by OA R = Et, 74% Mechanism: O. Baudoin, Chem. Eur. J., 2007, 13, 792. O. Baudoin, Angew. Chem., Int. Ed., 2003, 42, 5736.
53 Common C H activation: Direct C C bond formation triggered by OA For other computationally mechanistic studies of CMD, see: (a) A. M. Echavarren, J. Am. Chem. Soc., 2006, 128, 1066; (b) K. Fagnou, J. Am. Chem. Soc., 2006, 128, O. Baudoin, J. Am. Chem. Soc., 2008, 130,
54 Common C H activation: Direct C C bond formation triggered by OA K. Fagnou, J. Am. Chem. Soc., 2007, 129, K. Fagnou and O. Baudoin, J. Am. Chem. Soc., 2010, 132, H. Ohno, Org. Lett., 2008, 10, 1759.
55 Common C H activation: Direct C C bond formation triggered by OA K. Fagnou, J. Am. Chem. Soc., 2007, 129, K. Fagnou and O. Baudoin, J. Am. Chem. Soc., 2010, 132, H. Ohno, Org. Lett., 2008, 10, 1759.
56 Common C H activation: Direct C C bond formation triggered by OA K. Fagnou, J. Am. Chem. Soc., 2010, 132,
57 Common C H activation: Direct C C bond formation triggered by C-H cleavage C-H arylation O. Daugulis, J. Am. Chem. Soc., 2005, 127, Also see: E. J. Corey, Org. Lett., 2006, 8, 3391.
58 Common C H activation: Direct C C bond formation triggered by C-H cleavage Silver-free condition O. Daugulis, J. Am. Chem. Soc., 2010, 132, 3965.
59 Common C H activation: Direct C C bond formation triggered by C-H cleavage Silver-free condition O. Daugulis, J. Am. Chem. Soc., 2010, 132, 3965.
60 Common C H activation: Direct C C bond formation triggered by C-H cleavage Silver-free condition O. Daugulis, J. Am. Chem. Soc., 2010, 132, 3965.
61 Common C H activation: Direct C C bond formation triggered by C-H cleavage J.-Q. Yu, J. Am. Chem. Soc. 2012, 134, 18570
62 Common C H activation: Direct C C bond formation triggered by C-H cleavage Previous achievement J.-Q. Yu, J. Am. Chem. Soc. 2012, 134, 18570
63 Common C H activation: Direct C C bond formation triggered by C-H cleavage J.-Q. Yu, Science 2014, 343, 1216
64 Common C H activation: Direct C C bond formation triggered by C-H cleavage J.-Q. Yu, Science 2014, 343, 1216
65 Common C H activation: Direct C C bond formation triggered by C-H cleavage Chen, G. Angew. Chem. Int. Ed. 2011, 50, For the alkylation using alkyl iodide, see : J. Am. Chem. Soc. 2013, 135, % 17-82% Chen, G. J. Am. Chem. Soc. 2012, 134, 3
66 Common C H activation: Direct C C bond formation triggered by C-H cleavage C-H alkylation J.-Q. Yu, J. Am. Chem. Soc., 2006, 128,
67 Common C H activation: Direct C C bond formation triggered by C-H cleavage C-H alkylation J.-Q. Yu, J. Am. Chem. Soc., 2006, 128,
68 Common C H activation: Direct C C bond formation triggered by C-H cleavage C-H alkylation J.-Q. Yu, J. Am. Chem. Soc., 2006, 128,
69 Common C H activation: Direct C C bond formation triggered by C-H cleavage J.-Q. Yu, Angew. Chem., Int. Ed., 2008, 47, BX n = BPin, base = NaHCO 3 (3 eq.), additive = DMSO (0.4 eq) Yield = 60% BX n = BF 3 K, base = Li 2 CO 3 (3 eq.), additive = DMF (0.1 ml) Yield = 74% J.-Q. Yu, J. Am. Chem. Soc. 2011, 133, 19598
70 Common C H activation: Direct C C bond formation triggered by C-H cleavage J.-Q. Yu, Angew. Chem., Int. Ed., 2008, 47, BX n = BPin, base = NaHCO 3 (3 eq.), additive = DMSO (0.4 eq) Yield = 60% BX n = BF 3 K, base = Li 2 CO 3 (3 eq.), additive = DMF (0.1 ml) Yield = 74% J.-Q. Yu, J. Am. Chem. Soc. 2011, 133, 19598
71 Common C H activation: Direct C C bond formation triggered by C-H cleavage J.-Q. Yu, Angew. Chem., Int. Ed., 2008, 47, R = Aryl: BX n = BPin, base = NaHCO 3, solv = tamyl-oh R = vinyl: BX n = BPin, base = NaHCO 3, solv = THF R = alkyl: BX n = BF 3 K, base = Li 2 CO 3, solv = THF L27 = J.-Q. Yu, J. Am. Chem. Soc. 2011, 133, 19598
72 Common C H activation: Direct C C bond formation triggered by C-H cleavage Previous work J.-Q. Yu & Blackmond, D. G, J. Am. Chem. Soc. 2012, 134, J.-Q. Yu, Nature Chemistry 2014, 6, 146. BX n = BPin, base = NaHCO 3 (3 eq.), additive = DMSO (0.4 eq) Yield = 60% J.-Q. Yu, J. Am. Chem. Soc. 2011, 133, 19598
73 Common C H activation: Direct C C bond formation triggered by C-H cleavage J.-Q. Yu, J. Am. Chem. Soc., 2007, 129, 3510
74 Common C H activation: Direct C C bond formation triggered by C-H cleavage J.-Q. Yu, J. Am. Chem. Soc., 2008, 130, 7190.
75 Common C H activation: Direct C C bond formation triggered by C-H cleavage J.-Q. Yu, J. Am. Chem. Soc., 2010, 132, J.-Q. Yu, J. Am. Chem. Soc., 2010, 132, R = COOEt, 90% R = COOH, 69% M. S. Sanford, J. Am. Chem. Soc. 2011, 133, 6541.
76 Common C H activation: Direct C C bond formation triggered by C-H cleavage J.-Q. Yu, J. Am. Chem. Soc., 2010, 132, J.-Q. Yu, J. Am. Chem. Soc., 2010, 132, R = COOEt, 90% R = COOH, 69% See: Ishii, Y. Molecules 2010, 15, 1487 J.-Q. Yu, Angew. Chem. Int. Ed. 2013, 53, 2683 M. S. Sanford, J. Am. Chem. Soc. 2011, 133, 6541.
77 Common C H activation: Direct C C bond formation triggered by C-H cleavage J.-Q. Yu, J. Am. Chem. Soc., 2010, 132,
78 Content 1 Allylic C H activation 2 Benzylic C H activation Palladiumcatalyzed sp 3 C H activation 3 4 Common sp 3 C H activation: Direct C X bond formation Common sp 3 C H activation: Direct C C bond formation 5 Summary
79 Content 1 Allylic C H activation 2 Benzylic C H activation Palladiumcatalyzed sp 3 C H activation 3 4 Common sp 3 C H activation: Direct C X bond formation Common sp 3 C H activation: Direct C C bond formation 5 Summary
80 Summary via several pathways to construct synthetically useful C C/C X bonds. Palladiumcatalyzed sp 3 C H activation allylic sp3 C H bonds: pre-coordination of the Pd faciltate the activation non-allylic sp3 C H bonds: Pd(II)/Pd(0) and Pd(II)/Pd(IV), heteroatom DG play crucial roles tremendous challenge ahead lower catalyst loadings milder conditions site-selectivity / broader C-H bonds scope useful enantioselectivity
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84 Common C H activation: Direct C C bond formation triggered by C-H cleavage E. J. Corey, Org. Lett., 2006, 8, 3391.
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