Effect of Bronsted Acids and Bases, and Lewis Acid (Sn(2+)) on the Regiochemistry of the Reaction of Amines with Trifluoromethyl-β-diketones: Reaction of 3-Aminopyrrole to Selectively Produce Regioisomeric 1H-Pyrrolo[3,2-b]pyridines.
De Rosa, Michael; Arnold, David; Hartline, Douglas; Truong, Linda; Verner, Roman; Wang, Tianwei; Westin, Christian; The Journal of organic chemistry 80 (2015) 12288–12299; doi:10.1021/acs.joc.5b02192

data_4036493
_publ_section_title
;
 Effect of Bronsted Acids and Bases, and Lewis Acid (Sn(2+)) on the
 Regiochemistry of the Reaction of Amines with
 Trifluoromethyl-\b-diketones: Reaction of 3-Aminopyrrole to Selectively
 Produce Regioisomeric 1H-Pyrrolo[3,2-b]pyridines.
;
_journal_issue                   24
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              12288
_journal_page_last               12299
_journal_paper_doi               10.1021/acs.joc.5b02192
_journal_volume                  80
_journal_year                    2015
_chemical_formula_moiety         '2(C27 H21 B O2)'
_chemical_formula_sum            'C54 H42 B2 O4'
_chemical_formula_weight         172.55
_chemical_name_common            12
_chemical_name_systematic
(Z)-3-(Diphenylboryloxy)-1,3-diphenylprop-2-en-1-one
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2015-08-31
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_cell_angle_alpha                76.874(7)
_cell_angle_beta                 81.153(9)
_cell_angle_gamma                80.376(8)
_cell_formula_units_Z            4
_cell_length_a                   8.109(3)
_cell_length_b                   12.250(5)
_cell_length_c                   21.727(9)
_cell_measurement_reflns_used    3200
_cell_measurement_temperature    298
_cell_measurement_theta_max      23.501
_cell_measurement_theta_min      2.313
_cell_volume                     2057.2(14)
_computing_data_collection       'SMART v5.625 (Bruker, 2001)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_diffrn_ambient_temperature      298
_diffrn_measured_fraction_theta_full 0.923
_diffrn_measured_fraction_theta_max 0.884
_diffrn_measurement_device_type  'Bruker SMART APEX'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0648
_diffrn_reflns_av_unetI/netI     0.1096
_diffrn_reflns_Laue_measured_fraction_full 0.923
_diffrn_reflns_Laue_measured_fraction_max 0.884
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            16152
_diffrn_reflns_point_group_measured_fraction_full 0.923
_diffrn_reflns_point_group_measured_fraction_max 0.884
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.426
_diffrn_reflns_theta_min         1.723
_diffrn_source_current           32.0
_diffrn_source_power             1.6
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_T_max  1.00
_exptl_absorpt_correction_T_min  0.601640
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS was used for absorption correction.
R(int) was 0.1062 before and 0.0780 after correction.
The Ratio of minimum to maximum transmission is 0.6016.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.254
_exptl_crystal_description       block
_exptl_crystal_F_000             816
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.764
_refine_diff_density_min         -0.481
_refine_diff_density_rms         0.142
_refine_ls_extinction_coef       0.083(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.433
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     542
_refine_ls_number_reflns         9144
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.433
_refine_ls_R_factor_all          0.2133
_refine_ls_R_factor_gt           0.1655
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.2000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.4455
_refine_ls_wR_factor_ref         0.4658
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4725
_reflns_number_total             9144
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo5b02192_si_003.cif
_cod_data_source_block           mxd19s
_cod_original_cell_volume        2057.1(13)
_cod_database_code               4036493
_shelx_estimated_absorpt_t_max   0.991
_shelx_estimated_absorpt_t_min   0.983
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C7(H7), C8(H8), C11(H11), C12(H12), C13(H13),
 C14(H14), C15(H15), C17(H17), C18(H18), C19(H19), C20(H20), C21(H21), C23(H23),
  C24(H24), C25(H25), C26(H26), C27(H27), C30(H30), C31(H31), C32(H32),
 C33(H33), C34(H34), C35(H35), C38(H38), C39(H39), C40(H40), C41(H41), C42(H42),
  C44(H44), C45(H45), C46(H46), C47(H47), C48(H48), C50(H50), C51(H51),
 C52(H52), C53(H53), C54(H54)
;
_shelx_res_checksum              92812
_shelx_hkl_checksum              45458
_shelx_shelxl_version_number     2014/7
_olex2_submission_original_sample_id mxd19
_olex2_submission_special_instructions 'No special instructions were received'